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Total Synthesis Of (+)-daphmanidin E.

M. E. Weiss, E. Carreira
Published 2011 · Chemistry, Medicine

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9-16 1) 1.3-propanediol, pTsOH (10 mol%), PhH, reflux; then pTsOH (10 mol%), acetone, 50°C 2) KHMDS, 2-(NTf2)-pyridine, THF, -40°C 3) 1, 9-BBN, AsPh3 (16 mol%), [Pd2(dba)3]/CHCl3 (2 mol%), K3PO4, DMF/THF/H2O, 45°C 4) BH3•SMe2, THF, rt; then NaBO3•4 H2O; then DIBAL-H, THF, -25°C 5) pTsOH (5 mol%), acetone, 50°C 6) BzCl, pyridine, DMAP (cat.), CH2Cl2, rt 7) KHMDS, [18]-crown-6, 2, THF, -20°C 8) nonane, 155°C
This paper references
10.1021/CR950019Y
Sequencing Reactions with Samarium(II) Iodide.
G. Molander (1996)
10.1021/JA01022A059
New methods for the oxidation of aldehydes to carboxylic acids and esters
E. Corey (1968)
For examples , see a ) A . Rimkus , N . Sewald , Synthesis 2004 , 135 – 146 ; b ) H . Sch  fer , D
J. C. Martin D. B. Dess
10.1016/J.TETLET.2004.01.090
Convenient switching of 7-endo/6-exo radical cyclization
A. Kamimura (2004)
10.1055/S-1999-2802
Chemistry of Insect Antifeedants from Azadirachta indica (Part 22): Functionalisation of the Decalin Fragment of Azadirachtin via a Claisen Rearrangement Reaction
S. Ley (1999)
10.1021/jo00286a026
Sodium perborate: a mild and convenient reagent for efficiently oxidizing organoboranes
G. Kabalka (1989)
10.1002/anie.200907033
Chemoenzymatic synthesis and application of bicyclo[2.2.2]octadiene ligands: increased efficiency in rhodium-catalyzed asymmetric conjugate additions by electronic tuning.
Y. Luo (2010)
10.1021/JO00075A049
Stereocontrolled formation of octahydro-1H-pyrrolo[2,3-d]carbazoles by reductive cyclization: total synthesis of (.+-.)-N-benzylaspidospermidine
Nora Benchekroun-Mounir (1993)
For hydroboration of a trisubstituted olefin embedded in a bicyclo [ 2 . 2 . 2 ] octane system
N. Kanoh
10.1021/JA054316O
7-endo radical cyclizations catalyzed by titanocene(III). Straightforward synthesis of terpenoids with seven-membered carbocycles.
J. Justicia (2005)
10.1021/JO071126I
Lewis acid-promoted conjugate addition of dienol silyl ethers to nitroalkenes: synthesis of 3-substituted azepanes.
S. Denmark (2007)
10.1246/BCSJ.55.1498
The Reaction of Bis(dimethylglyoximato)(pyridine)cobalt(I), Cobaloxime(I), with 2-(Allyloxy)ethyl Halides and the Photolysis of the Resulting Organo-cobaloximes
Masami Okabe (1982)
10.1021/ol9003405
Synthetic studies on daphnicyclidin A: enantiocontrolled construction of the BCD ring system.
S. Ikeda (2009)
For selected examples of cobalt-mediated alkyl-Heck coupling reactions
B. P. Branchaud (1988)
10.1002/anie.200902151
Samarium diiodide mediated reactions in total synthesis.
K. Nicolaou (2009)
10.1021/ol902373m
Asymmetric construction of rings A-D of daphnicyclidin-type alkaloids.
Travis B. Dunn (2009)
10.1016/J.TET.2008.06.091
Total synthesis of (±)-stemonamide, (±)-isostemonamide, (±)-stemonamine, and (±)-isostemonamine using a radical cascade
Tsuyoshi Taniguchi (2008)
10.1055/S-2001-12340
An Efficient and Selective Method for Hydrolysis of Acetonides
Xiangshu Xiao (2001)
10.1021/NP0503799
Daphmanidins E and F, alkaloids from Daphniphyllum teijsmannii.
H. Morita (2006)
10.1021/JO00895A030
Olefin synthesis. Rate enhancement of the elimination of alkyl aryl selenoxides by electron-withdrawing substituents
K. Sharpless (1975)
10.1016/S0040-4039(00)80043-X
Alkyl-alkenyl cross coupling via alkyl cobaloxime radical chemistry.An alkyl equivalent to the heck reaction compatible with common organic functional groups
B. Branchaud (1988)
10.1016/0040-4039(96)00915-X
UNCATALYZED CONJUGATE ADDITIONS OF DIORGANOZINCS IN N-METHYLPYRROLIDINONE
C. K. Reddy (1996)
10.1021/OL0488338
Efficient Cu-catalyzed asymmetric conjugate additions of alkylzinc reagents to aromatic and aliphatic acyclic nitroalkenes.
Dawn M. Mampreian (2004)
10.1039/B813006J
The Daphniphyllum alkaloids.
J. Kobayashi (2003)
For selected examples of cobalt - mediated alkyl - Heck coupling reactions , see a ) B . P . Branchaud
M. S. Meier (1969)
10.1021/CR00026A008
Transition Metal-Promoted Free-Radical Reactions in Organic Synthesis: The Formation of Carbon-Carbon Bonds
J. Iqbal (1994)
10.1021/JO00870A052
Organoselenium chemistry. A facile one-step synthesis of alkyl aryl selenides from alcohols
P. A. Grieco (1976)
10.1039/P19920003193
Acyl radical cyclizations in synthesis. Part 4. Tandem processes: the 7-endo/5-exo serial cyclization approach to enantiomerically pure bicyclo[5.3.0]decan-2-ones
D. Batty (1992)
10.1021/JO00170A070
Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones
D. Dess (1983)
10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N
The B-Alkyl Suzuki-Miyaura Cross-Coupling Reaction: Development, Mechanistic Study, and Applications in Natural Product Synthesis A list of abbreviations can be found at the end of the article.
S. Chemler (2001)
10.1021/JO00388A031
Stereospecific skeletal rearrangement reactions in bridgehead-substituted bicyclo[2.2.2] systems under neutral conditions
D. Hua (1987)
10.1002/ANGE.200902151
Samariumdiiodid-vermittelte Reaktionen in der Totalsynthese
K. C. Nicolaou (2009)
10.1021/CR00006A006
Radical reactions in natural product synthesis
C. Jasperse (1991)
10.1021/ol102961x
Cascade cyclization, dipolar cycloaddition to bridged tricyclic amines related to the Daphniphyllum alkaloids.
I. Coldham (2011)
10.1016/S0040-4039(00)88238-6
Dimethylboron bromide and diphenylboron bromide. Acetal and ketal cleavage. Cleavage of MEM, MOM, and MTM ethers.
Yvan Quindon (1983)
10.1002/CBER.19390720708
Para‐Brückenbildung beim Succinylo‐bernsteinsäure‐äthylester, I. Mitteil.: Bildung von Bicyclo‐[1.2.2]‐heptan‐, Bicyclo‐[2.2.2]‐octan‐ und Bicyclo‐[3.2.2]‐nonan‐Systemen
P. C. Guha (1939)
10.1039/CS9881700361
Simonsen Lecture. Cobalt-mediated radical reactions in organic synthesis
G. Pattenden (1988)
10.1021/JO00125A067
TRIPHENYLTIN)COBALOXIME AS A REAGENT FOR RADICAL GENERATION FROM BROMIDES
M. Tada (1995)
10.1002/0471264180.OS074.07
Pyridine‐Derived Triflating Reagents: N‐(2‐Pyridyl)‐Triflimide and N‐(5‐Chloro‐2‐Pyridyl)Triflimide
D. Comins (1997)
10.1002/CBER.19691020727
Organometallderivate des Bis(dimethylglyoximato)-kobalts
G. Schrauzer (1969)
10.1002/1521-3757(20011217)113:24<4676::AID-ANGE4676>3.0.CO;2-B
DieB-Alkyl-Suzuki-Miyaura-Kreuzkupplung: Entwicklung, Untersuchungen zum Mechanismus und Anwendungen in der Naturstoffsynthese
S. Chemler (2001)
10.1021/JA075245R
Intramolecular Heck reactions of unactivated alkyl halides.
L. Firmansjah (2007)
10.1021/ja803158y
Total Synthesis of (±)-Actinophyllic Acid
C. Martin (2008)
10.1039/C39870000166
Cobalt-mediated cyclization of amino acid derivatives. Application to the kainoids
J. Baldwin (1987)
10.1016/0040-4020(94)01100-E
Enantioselective conjugate addition of primary dialkylzinc reagents to 2-aryl- and 2-heteroaryl-nitroolefins mediated by titanium-TADDOLates preparation of enantioenriched 2-aryl-alkylamines
H. Schaefer (1995)
10.1055/S-2001-18700
The Nitro Group in Organic Synthesis
F. Heaney (2004)



This paper is referenced by
10.1016/J.TETLET.2015.04.091
Olefin difunctionalizations via visible light photocatalysis
M. Cao (2015)
10.1021/JO301533F
Synthesis of the tetracyclic core (ABCE rings) of daphenylline.
B. Fang (2012)
10.1016/J.TET.2014.12.033
Molecular diversity from aromatics. Cycloaddition of cyclohexa-2,4-dienones, ring-closing metathesis and sigmatropic shifts: a general and stereoselective route to novel spirocarbocyclics
V. Singh (2015)
10.1039/c4cs00523f
Recent advances in heterobimetallic catalysis across a "transition metal-tin" motif.
Debjit Das (2015)
10.1039/d0cc05580h
Selective photoredox decarboxylation of α-ketoacids to allylic ketones and 1,4-dicarbonyl compounds dependent on cobaloxime catalysis.
H. Zhang (2020)
10.1039/c3np70115h
Strategies towards the synthesis of calyciphylline A-type Daphniphyllum alkaloids.
B. Kang (2014)
10.1021/acs.chemrev.6b00833
Methods Utilizing First-Row Transition Metals in Natural Product Total Synthesis.
Joshua E Zweig (2017)
10.1016/J.CHEMPR.2017.04.007
A Radical Cascade Enabling Collective Syntheses of Natural Products
Xiao-bei Wang (2017)
10.1039/d0ob00278j
Asymmetric copper-catalyzed conjugate additions of organometallic reagents in the syntheses of natural compounds and pharmaceuticals.
Denisa Vargová (2020)
10.1021/acs.orglett.7b00230
Synthesis of the ABC Tricyclic System of Daphnicyclidin A.
J. Li (2017)
10.1039/C4QO00311J
Enantioselective synthesis of bicyclo[2.2.2]octane-1-carboxylates under metal free conditions
Ying-zi Li (2015)
10.1016/J.TETASY.2017.10.013
Review on asymmetric synthetic methodologies for chiral isoquinuclidines; 2008 to date
M. Faisal (2017)
10.1021/acs.orglett.5b02581
Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (-)-Huperzine N.
C. Bosch (2015)
10.1021/cr500127b
Four-membered ring-containing spirocycles: synthetic strategies and opportunities.
E. Carreira (2014)
10.1002/anie.201505126
Pentafulvene for the synthesis of complex natural products: total syntheses of (±)-pallambins A and B.
C. Ebner (2015)
10.1039/c7cs00226b
Visible light-induced transition metal-catalyzed transformations: beyond conventional photosensitizers.
Marvin Parasram (2017)
10.1021/ol5005092
Stereocontrolled synthesis of the tricyclic ABC ring system of daphnicyclidin A.
D. Williams (2014)
10.1021/ol3002267
Expedient construction of the [7-5-5] all-carbon tricyclic core of the Daphniphyllum alkaloids daphnilongeranin B and daphniyunnine D.
Benjamin Darses (2012)
10.1002/asia.201200625
Rapid construction of the [6-6-6-5] tetracyclic skeleton of the Daphniphyllum alkaloid daphenylline.
H. Li (2012)
10.1021/acs.orglett.5b03356
A Unified Strategy to Plakortin Pentalenes: Total Syntheses of (±)-Gracilioethers E and F.
Stefan A. Ruider (2016)
10.1016/J.TET.2017.09.035
Synthesis of the AE bicyclic of Daphniphyllum alkaloid yuzurine
Y. Liu (2017)
10.1002/anie.201305822
Total synthesis of (+)-crotogoudin.
S. Breitler (2013)
10.1021/ol4034868
Rapid Access to the Heterocyclic Core of the Calyciphylline A and Daphnicyclidin A-Type Daphniphyllum Alkaloids via Tandem Cyclization of a Neutral Aminyl Radical
A. A. Ibrahim (2014)
10.1002/asia.201403061
Expedient construction of the [5-6-7] tricyclic core of calyciphylline a-type alkaloids.
J. Guo (2015)
10.1016/B978-0-08-097742-3.00419-5
4.13 Radical Cyclizations and Sequential Radical Reactions
B. M. Loertscher (2014)
10.1021/acs.joc.6b00638
Strategies toward the Total Synthesis of Calyciphylline B-type Alkaloids: A Computational Perspective Aided by DFT Analysis.
A. K. Chattopadhyay (2016)
10.1021/acs.orglett.7b00035
Synthesis of the Tetracyclic ABCD Ring Domain of Calyciphylline A-Type Alkaloids via Reductive Radical Cyclizations.
Guilhem Coussanes (2017)
10.1002/9783527671304.CH14
Domino Reactions in the Total Synthesis of Natural Products
Svenia‐C. Duefert (2013)
10.1016/J.TET.2016.11.030
A boron-based Ireland-Claisen approach to the synthesis of pordamacrine A
Curtis A. Seizert (2017)
10.1021/ja503899t
The Daphniphyllum Alkaloids: Total Synthesis of (−)-Calyciphylline N
Artem Shvartsbart (2015)
10.1002/IJCH.201700127
Natural Products Synthesis: A Personal Retrospective and Outlook
E. Carreira (2018)
10.1002/9783527664573.CH14
Applications to the Synthesis of Natural Products
B. Calvo (2014)
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