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Selective Deoxygenation Of Allylic Alcohol: Stereocontrolled Synthesis Of Lavandulol.

H. Kim, L. Su, H. Jung, S. Koo
Published 2011 · Medicine, Chemistry

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Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl(2)-catalyzed reduction with LiBHEt(3). (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)(4)-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
This paper references
10.1055/S-2003-38057
A New Synthesis of Lavandulol via Indium/Palladium-Mediated Umpolung of Vinyloxirane
S. Araki (2003)
10.1021/jo802064c
Ring-expansion protocol: preparation of synthetically versatile dihydrotropones.
Young-Sun Do (2009)
10.1016/S0040-4039(00)02347-9
Identification and synthesis of the sex pheromone of the vine mealybug, Planococcus ficus
Diane M. Hinkens (2001)
10.1039/C39800000683
Synthesis of (±)-lavandulol and its related homoallylic alcohol via allyl transfer from sulphur to tin
Y. Ueno (1980)
10.1039/B511067J
Preparation of 1,4-hydrobenzoquinones by the PCC/SiO2-promoted double oxidation of 3-cyclohexene-1,2-diols.
H. J. Kim (2005)
10.1021/JO00129A030
ENANTIO- AND DIASTEREOSELECTIVE PROTONATION OF PHOTODIENOLS : TOTAL SYNTHESIS OF (R)-(-)-LAVANDULOL
O. Piva (1995)
10.1021/jo702303a
General preparation and controlled cyclization of acyclic terpenoids.
Jinchul Kuk (2008)
10.1246/CL.1987.707
Regio- and Stereoselective Synthesis of Allylic and Homoallylic Alcohols by the Reductive Desulfonylation of Allylic Sulfone Derivatives. Application to the Syntheses of (±)-Lavandulol and Isolavandulol
K. Inomata (1987)
10.1016/S0040-4020(01)80712-2
Highly efficient terpenoid pheromone syntheses via regio and stereocontrolled processing of allyllithiums generated by reductive lithiation of allyl phenyl thioethers
D. W. Mccullough (1991)
10.1055/S-1998-1960
Asymmetric α-Alkylation of α,β-Unsaturated Esters. Application to the Synthesis of (R)-Lavandulol, (R)-Sesquilavandulol and Related Trifluoromethyl Compounds
S. Faure (1998)
10.1021/JO990161P
Synthesis of Farnesol Analogues through Cu(I)-Mediated Displacements of Allylic THP Ethers by Grignard Reagents.
Mark F. Mechelke (1999)
10.1016/J.TET.2004.04.023
Grob-type fragmentation of a carvone derived β-hydroxymesylate: application to the synthesis of chiral lavandulol derivatives
G. Mehta (2004)
10.1002/HLCA.200790042
Reactions of Allyl Alcohols of the Pinane Series and of Their Epoxides in the Presence of Montmorillonite Clay
I. Il’ina (2007)
10.1021/JO00245A043
Diastereoselective alkylation of 3-acylimidazolidin-2-ones: synthesis of (R)- and (S)-lavandulol
G. Cardillo (1988)
10.1002/chin.198535288
GENERAL CHIRAL ROUTE TO IRREGULAR MONOTERPENES VIA A COMMON INTERMEDIATE: SYNTHESES OF (S)-LAVANDULOL, CIS(1S,3R)-CHRYSANTHEMOL, (1R,2S)-ROTHROCKENE, AND (R)-SANTOLINATRIENE
S. Takano (1985)
10.1021/JO00974A034
Novel cyclization mediated by organocopper reagents
J. Katzenellenbogen (1972)



This paper is referenced by
10.1016/B978-0-444-62615-8.00007-2
Chapter 7 - Bioactive Natural Products from Enantiomeric Carvones
F. Macaev (2013)
10.1515/pac-2017-0501
Photocatalytic hydrogenolysis of allylic alcohols for rapid access to platform chemicals and fine chemicals
Y. Takada (2017)
10.1002/EJOC.201300657
Reductive Deoxygenation of Alcohols: Catalytic Methods Beyond Barton–McCombie Deoxygenation
J. M. Herrmann (2013)
10.1039/C5RA14775A
Ethers as hydrogen sources in BF3·OEt2 promoted reduction of diphenylmethyl alcohols, ethers and esters to hydrocarbons
Jiaqiang Li (2015)
10.1016/j.biortech.2011.11.038
Transformation of (±)-lavandulol and (±)-tetrahydrolavandulol by a fungal strain Rhizopus oryzae.
P. P. Daramwar (2012)
10.1002/EJOC.201200627
Synthesis of Coenzyme Q10
Eun-Taek Oh (2012)
10.1039/C5RA01545F
An unprecedented deoxygenation protocol of benzylic alcohols using bis(1-benzotriazolyl)methanethione
D. Kumar (2015)
10.1070/RC2014V083N04ABEH004383
Synthesis of hydroxy derivatives of limonene
O. Ardashov (2014)
Lavandulol – biological activity and synthesis
K. Ciołak (2014)
10.1007/s11144-013-0615-9
Opening of monoterpene epoxide to a potent anti-Parkinson compound of para-menthane structure over heterogeneous catalysts
Martina Štekrová (2013)
10.1002/SLCT.201601890
An Efficient Total Synthesis of (–)‐(R), (+)‐(S)‐Lavandulol Pheromones and Their Derivatives through Proline Catalyzed Asymmetric α‐Aminooxylation and [3,3] Claisen Rearrangement
V. A. Bhosale (2017)
10.1021/jo400884g
Divergent diastereoselective synthesis of iridomyrmecin, isoiridomyrmecin, teucrimulactone, and dolicholactone from citronellol.
Clara Fischman (2013)
10.1002/anie.201205143
Enantioselective total synthesis of the diterpene (+)-cubitene.
Kristina Simon (2012)
10.1016/J.MOLCATA.2015.09.021
Prins cyclization: Synthesis of compounds with tetrahydropyran moiety over heterogeneous catalysts
Martina Stekrova (2015)
10.1002/chem.201704099
Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2 : A Shortcut to (S)-(+)-Lavandulol.
Y. Takada (2017)
10.1016/J.TET.2015.06.105
Mechanically Activated Ring-Opening Reactions of N-acyl-1,2,3,4-Tetrahydroisoquinolines Derived From the Synthesis of Praziquantel Intermediate
Jingbo Yu (2015)
10.1021/acs.joc.6b02564
Nickel-Catalyzed Cross-Coupling of Allyl Alcohols with Aryl- or Alkenylzinc Reagents.
Bo Yang (2017)
10.1002/EJOC.201300520
A Synthesis of (–)‐(R)‐ and (+)‐(S)‐Lavandulol, (+)‐Lavandulyl 2‐Methylbutanoate, and (+)‐Lavandulyl Senecioate through Ortho­ester Johnson–Claisen Rearrangement
R. A. Fernandes (2013)
10.1002/ANGE.201205143
Enantioselektive Totalsynthese des Diterpens (+)‐Cubiten
Kristina Simon (2012)
10.1021/jo500027k
Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone.
Henry P. Pepper (2014)
10.1016/J.TET.2013.03.020
Regioselective and reductive cleavage of allyl ethers by NaBH4–HOAc
Zi-ping Lin (2013)
10.1002/chem.201805219
C3 and C6 Modification‐Specific OYE Biotransformations of Synthetic Carvones and Sequential BVMO Chemoenzymatic Synthesis of Chiral Caprolactones†
I. S. Issa (2019)
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