Online citations, reference lists, and bibliographies.
← Back to Search

A Formal Total Synthesis Of (+)-pinnatoxin A.

S. Sakamoto, H. Sakazaki, Koji Hagiwara, K. Kamada, Kento Ishii, T. Noda, Masayuki Inoue, M. Hirama
Published 2004 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
This paper references
10.1016/0040-4039(96)00753-8
Isolation and structure of pinnatoxin D, a new shellfish poison from the okinawan bivalve Pinna muricata
T. Chou (1996)
10.1002/ANIE.200352423
Total synthesis of microsclerodermin E.
Jidong Zhu (2003)
10.1016/0040-4039(95)01898-R
On the flexibility of allylic azides as synthetic intermediates
B. Trost (1995)
10.1002/ANIE.196506451
New Reactions of Alkylidenephosphoranes and their Preparative Uses. Part II. Alkylidenephosphoranes and Halogen Compounds
H. Bestmann (1965)
10.1002/1521-3757(20000901)112:17<3140::AID-ANGE3140>3.0.CO;2-G
Olefinmetathese und mehr
A. Fürstner (2000)
10.1021/JA00209A048
Selective hydride-mediated conjugate reduction of .alpha.,.beta.-unsaturated carbonyl compounds using [(Ph3P)CuH]6
W. S. Mahoney (1988)
10.1055/S-1999-2743
Synthetic Study of Pinnatoxin A: Intramolecular Diels-Alder Approach to the AG-ring
A. Ishiwata (1999)
10.1016/S0040-4020(01)00861-4
Assignment of the relative stereochemistry of the spirolides, macrocyclic toxins isolated from shellfish and from the cultured dinoflagellate Alexandrium ostenfeldii
M. Falk (2001)
10.1016/0040-4039(96)00752-6
Relative stereochemistry of pinnatoxin A, a potent shellfish poison from Pinna muricata
Tong Chou (1996)
10.1002/ANGE.19650771503
Neuere Methoden der präparativen organischen Chemie IV. Neue Reaktionen von Phosphinalkylenen und ihre präparativen Möglichkeiten II. Phosphinalkylene und Halogenverbindungen
H. Bestmann (1965)
10.1021/CR00032A009
Catalytic Asymmetric Dihydroxylation
H. Kolb (1994)
10.1021/AR960289I
Total Synthesis of Immunosuppressants: Unified Strategies Exploiting Dithiane Couplings and σ-Bond Olefin Constructions†
A. Smith (1998)
10.1039/B104200A
One-step assembling reaction to the pentacyclic acetal of pinnatoxins
Jun Ishihara (2001)
10.1016/S0040-4039(01)00478-6
Structural determination of pteriatoxins A, B and C, extremely potent toxins from the bivalve Pteria penguin
Noboru Takada (2001)
10.1021/JA00019A027
A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species
D. Dess (1991)
Kishi's group achieved the total synthesis of pinnatoxin A (3) and ent-3. They reported that only natural pinnatoxin A was toxic
J. A. Mccauley (1998)
10.1021/JO00067A002
Improved enantioselectivity in asymmetric dihydroxylations of terminal olefins using pyrimidine ligands
G. Crispino (1993)
10.1021/JA00823A052
Epoxynitrile cyclization. General method of ring formation
G. Stork (1974)
10.1021/OL990909Q
Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands.
M. Scholl (1999)
10.1039/C39950002159
Spirolides B and D, two novel macrocycles isolated from the digestive glands of shellfish
Tingmo Hu (1995)
10.3987/R-1987-01-0121
A convenient two-step synthesis of 3-allylcoumarins and their benzoderivatives
R. Mali (1987)
10.1021/JA00253A032
Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization
Y. Gao (1987)
10.1016/S0040-4039(97)01725-5
The first construction of the B,C,D-ring fragment of pinnatoxins via highly stereocontrolled acetallization
Tetsuya Sugimoto (1997)
10.1016/S0040-4039(01)91105-0
Preferential formation of 8-epi-prostaglandin f2α via the corresponding endoperoxide by a biomimetic cyclization
E. Corey (1984)
10.1055/S-1998-1742
Studies on the Stability of 1,7,9-Trioxadispiro[5.1.5.2]pentadecane System: The Common Tricyclic Acetal Moiety in Pinnatoxins
Jun Ishihara (1998)
10.1021/JA963066W
A Unified Total Synthesis of the Immunomodulators (−)-Rapamycin and (−)-27-Demethoxyrapamycin: Construction of the C(21−42) Perimeters
A. Smith (1997)
10.1016/S0040-4020(99)00387-7
Synthesis of bis-spiroacetal ring systems
M. Brimble (1999)
10.1055/S-1998-1648
Synthetic Study of Pinnatoxin A: Stereoselective Synthesis of the BCD-ring Unit, a Novel 6,5,6-Bis-spiroketal System
T. Noda (1998)
10.1021/JA00238A060
Total synthesis of (+)-phyllanthocin
A. B. Smith (1987)
10.1055/S-1999-2689
Synthesis of the B,C,D,E,F-Ring Fragment of Pinnatoxins
Tetsuya Sugimoto (1999)
10.1021/JA00068A102
A Dramatic Ligand Effect on the Relative Reactive Reactivites of Substituted Alkenes with Osmium Tetroxide
P. Andersson (1993)
10.1021/AR000114F
The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.
T. M. Trnka (2001)
10.5059/YUKIGOSEIKYOKAISHI.58.877
Total Synthesis of Pinnatoxin A
K. Nagasawa (2000)
10.1055/S-1998-1583
Chemical Manganese Dioxide (CMD), an Efficient Activated Manganese Dioxide. Application to Oxidation of Benzylic and Allylic Alcohols
T. Aoyama (1998)
10.1021/OL0168364
A stereoselective synthesis of the C10-C31 (BCDEF ring) portion of pinnatoxin A.
S. Nakamura (2001)
10.1016/S0040-4039(00)87440-7
Reductive ring openings of allyl-alcohol epoxides
J. M. Finan (1982)
10.1016/S0040-4039(00)95608-9
Protection of alcohols as their (p-methoxybenzyloxy)methyl ethers.
A. Kozikowski (1987)
10.1021/JA00346A071
A stereoselective synthesis of 1,3-diol derivatives and application to the ansa bridge of rifamycin S
W. C. Still (1983)
10.1002/ANGE.18910042108
Zur Beurtheilung der Kaffeesurrogate
C. Kornauth (1891)
10.1021/JA00108A043
PINNATOXIN A : A TOXIC AMPHOTERIC MACROCYCLE FROM THE OKINAWAN BIVALVE PINNA MURICATA
Daisuke Uemura (1995)
10.1016/0008-6215(95)00227-8
4,6-O-benzylidene-D-glucopyranose and its sodium salt: new data on their preparation and properties.
P. Barili (1995)
10.1016/S0040-4039(00)95181-5
A simple method of dethioacetalization
G. Stork (1989)
10.1021/JO01297A010
Quinone dehydrogenation. Oxidation of benzylic alcohols with 2,3-dichloro-5,6-dicyanobenzoquinone
H. D. Becker (1980)
10.1002/1521-3773(20000818)39:16<2891::AID-ANIE2891>3.0.CO;2-Q
Luminescent Mesoporous Molecular Materials Based on Neutral Tetrametallic Rectangles We gratefully acknowledge the U.S. National Science Foundation and the National Oceanic and Atmospheric Administration for financial support. Mass spectrometry was provided by the Washington University Mass Spectrom
Benkstein (2000)
10.1055/S-1999-2744
Synthetic Study of Pinnatoxin A: Intramolecular Alkylation Approach to the G-ring
Aiko Nitta (1999)
10.1016/S0040-4039(98)00221-4
Synthesis and NMR profiling of dioxabicyclo[3.2.1]octanes related to pinnatoxin D. Confirmation of the relative stereochemistry about rings E and F
B. Suthers (1998)
10.1021/JA00823A053
Ring size in epoxynitrile cyclization. General synthesis of functionally substituted cyclobutanes. Application to (+-)-grandisol
G. Stork (1974)
10.1016/S0040-4039(01)00480-4
Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata
Noboru Takada (2001)
10.1021/OL026605C
Synthesis of the C10-C22 bis-spiroacetal domain of spirolides B and D via iterative oxidative radical cyclization.
Daniel P Furkert (2002)
10.1016/S0040-4020(01)01134-6
Nitrile anion cyclizations
F. Fleming (2002)
10.1021/ja00433a040
Hydroboration. 43. Effect of structure on the reactivity of representative olefins toward hydroboration by 9-borabicyclo[3.3.1]nonane
H. Brown (1976)
10.1055/S-1979-28761
Esterification and Alkylation Reactions Employing Isoureas
L. Mathias (1979)
10.1021/JA00479A061
Olefin homologation with titanium methylene compounds
F. N. Tebbe (1978)



This paper is referenced by
10.1021/ja207385y
Total synthesis of the spirocyclic imine marine toxin (-)-gymnodimine and an unnatural C4-epimer.
Ke Kong (2011)
10.1039/C1SC00570G
Stereoselective heterocycle synthesis through a reversible allylic alcohol transposition and nucleophilic addition sequence
Youwei Xie (2011)
10.1039/c0np00066c
Marine natural products: synthetic aspects.
J. Morris (2011)
10.1002/9781118500354.CH3
Chemistry of pinnatoxins
P. Mabe (2015)
10.1002/CHIN.200516207
A Formal Total Synthesis of (+)‐Pinnatoxin A.
S. Sakamoto (2005)
10.1016/J.TETLET.2007.07.182
Studies toward the synthesis of pinnatoxins: the spiroimine fragment
C. Stivala (2007)
10.1039/B700307M
Synthesis of macrocyclic shellfish toxins containing spiroimine moieties.
P. D. O'Connor (2007)
10.1002/9781118651421.CH1
1. Organocopper Chemistry
B. Lipshutz (2013)
10.1021/OL0611548
Total synthesis and stereochemistry of pinnatoxins B and C.
F. Matsuura (2006)
10.1016/J.CCR.2005.10.020
The chemistry of the carbon–transition metal double and triple bond: Annual survey covering the year 2004
J. W. Herndon (2006)
10.1002/AJOC.201700164
Efficient Access to the Functionalized Bicyclic Pharmacophore of Spirolide C by Using a Selective Diels–Alder Reaction
Hiroshi Tsuchikawa (2017)
10.2183/pjab.92.290
Total synthesis and related studies of large, strained, and bioactive natural products
M. Hirama (2016)
10.3987/REV-08-637
Biologically Active Marine Natural Products
Daisuke Uemura (2009)
10.1021/ol201448h
Effect of counterion structure on rates and diastereoselectivities in α,β-unsaturated iminium-ion Diels-Alder reactions.
D. Marcoux (2011)
10.1002/EJOC.201000842
Marine Toxins with Spiroimine Rings: Total Synthesis of Pinnatoxin A.
S. Beaumont (2010)
10.1002/chem.201804972
An Approach towards the Synthesis of the Spiroimine Fragment of 13-Desmethylspirolide C and Gymnodimine A.
Alexandre Guthertz (2019)
10.1111/jnc.13995
Cyclic imine toxins from dinoflagellates: a growing family of potent antagonists of the nicotinic acetylcholine receptors
J. Molgó (2017)
10.1055/S-0037-1610281
Synthetic Versatility of Lipases: Application for Si–O Bond Formation and Cleavage
P. B. Brondani (2019)
10.1002/anie.200802729
Total synthesis of pinnatoxin A.
S. Nakamura (2008)
10.1007/978-1-4020-6091-5_12
Recent Applications Of Alkene Metathesis For Fine Chemical And Supramolecular System Synthesis
F. Požgan (2007)
10.1002/9783527335855.MARPROD232
23-2 Mollusks–2
Jean-Michel Kornprobst (2014)
10.1016/J.TETLET.2006.08.083
Synthesis of the A,G-spiroimine of pinnatoxins by a microwave-assisted tandem Claisen-Mislow-Evans rearrangement
M. Pelc (2006)
PROGRESS IN THE TOTAL SYNTHESIS OF SPIROLIDE C AND A MODEL SYSTEM OF A KEY DIELS-ALDER MACROCYCLIZATION
Anthony F. Bencivenga (2013)
10.1016/J.CCR.2006.02.031
Transition metals in organic synthesis : Highlights for the year 2004
B. Soederberg (2006)
10.1021/ja201254c
Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.
R. Aráoz (2011)
10.1016/J.TETASY.2008.04.013
Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence
S. Nakamura (2008)
10.1016/B978-0-08-096805-6.00015-2
Six-Membered Ring Systems
J. Hepworth (2011)
10.1002/chem.201804977
Synthetic Studies on Spirolides A and B: Formation of the Upper Carbon Framework Based on a Lewis Acid Template-Catalyzed Diels-Alder Reaction.
Jun Ishihara (2019)
10.1002/AJOC.201800074
Stereoselective Construction of Cisoidal Bisspiroacetal Frameworks through Magnesium Coordination of the Bilateral Acetal Oxygen Atoms
Yoshifumi Yasukawa (2018)
10.1021/ol402017x
Convergent access to bis-spiroacetals through a Sila-Stetter-ketalization cascade.
Jessica Labarre-Lainé (2013)
10.1201/B16806-7
Cyclic Imine Neurotoxins Acting on Muscarinic and Nicotinic Acetylcholine Receptors
J. Molgó (2014)
10.1007/7081_2015_151
Synthesis of Macrocycles Other than Peptides by Metathesis
A. Gradillas (2015)
See more
Semantic Scholar Logo Some data provided by SemanticScholar