A synthesis of the carbocyclic core of maoecrystal v

Kiel E. Lazarski; Dennis X. Hu; Charlotte L. Stern; Regan J. Thomson

doi:10.1021/ol101025r

A synthesis of the carbocyclic core of maoecrystal v

Kiel E. Lazarski, Dennis X. Hu, Charlotte L. Stern, Regan J. Thomson

Chemistry

Research output: Contribution to journal › Article › peer-review

43 Scopus citations

Abstract

An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels-Alder reaction to forge the two contiguous quaternary stereocenters.

Original language	English (US)
Pages (from-to)	3010-3013
Number of pages	4
Journal	Organic Letters
Volume	12
Issue number	13
DOIs	https://doi.org/10.1021/ol101025r
State	Published - Jul 2 2010

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol101025r

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title = "A synthesis of the carbocyclic core of maoecrystal v",

abstract = "An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels-Alder reaction to forge the two contiguous quaternary stereocenters.",

author = "Lazarski, {Kiel E.} and Hu, {Dennis X.} and Stern, {Charlotte L.} and Thomson, {Regan J.}",

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journal = "Organic Letters",

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T1 - A synthesis of the carbocyclic core of maoecrystal v

AU - Lazarski, Kiel E.

AU - Hu, Dennis X.

AU - Stern, Charlotte L.

AU - Thomson, Regan J.

PY - 2010/7/2

Y1 - 2010/7/2

N2 - An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels-Alder reaction to forge the two contiguous quaternary stereocenters.

AB - An approach toward the synthesis of the complex polycyclic diterpene maoecrystal V (1) is described. Construction of the advanced tetracyclic core structure (i.e., 19) was achieved in 13 steps from 3,3-dimethylcyclohexanone (6) by employing a stereoselective Nazarov cyclization followed by a Diels-Alder reaction to forge the two contiguous quaternary stereocenters.

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U2 - 10.1021/ol101025r

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A synthesis of the carbocyclic core of maoecrystal v

Abstract

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CCDC 813825: Experimental Crystal Structure Determination

CCDC 813821: Experimental Crystal Structure Determination

CCDC 813822: Experimental Crystal Structure Determination

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A synthesis of the carbocyclic core of maoecrystal v

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 813825: Experimental Crystal Structure Determination

CCDC 813821: Experimental Crystal Structure Determination

CCDC 813822: Experimental Crystal Structure Determination

Cite this