Recent Progress in the Total Synthesis of Dolabellane and Dolastane Diterpenes

Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 243)

Abstract

The isolation, structure and total synthesis of members of four classes of diterpenes has been summarized. Dolabellanes, neodolabellanes, dolastanes and neodolastanes are structurally related bi- or tricyclic diterpenes. Dolabellanes belong to a continuously growing class of diterpenes being isolated from marine and terrestrial sources. The published work on isolation and synthesis since 1998 has been summarized. Neodolabellanes represent a scarce class of diterpenes that have been isolated exclusively from marine sources. 5-7-6-tricyclic diterpenes classified as dolastanes have been isolated mainly from marine sources. The intense research devoted to the total synthesis of these diterpenes between 1986 and 1993 has been reviewed. Guanacastepenes have been isolated from fungi. These diterpenes are classified as neodolastanes and recently completed syntheses as well as synthetic approaches have been summarized.

Keywords

Diterpene Total Synthesis Natural Product Dolabellane Dolastane Guanacastepene 

List of Abbreviations

DCE

Dichloroethane

DIBAH

Diisobutylaluminium hydride

DPPB

Bis(diphenylphosphino)butane

Cy

Cyclohexyl

DBA

trans,trans-Dibenzylideneacetone

DMDO

Dimethyldioxirane

DMP

2,2-Dimethoxypropane

ED50

Effective dose 50%

HWE

Horner-Wadsworth-Emmons

LAH

Lithium aluminium hydride

NMO

4-Methylmorpholine N-oxide

NOE

Nuclear Overhauser effect

RCM

Ring closing metathesis

SAE

Sharpless asymmetric epoxidation

TBS

tert-Butyldimethylsilyl

TEMPO

2,2,6,6-Tetramethyl-1-piperidinyloxy

TES

Triethylsilyl

TFP

Tri-2-furylphospine

TLC

Thin layer chromatography

TPAP

Tetrapropylammonium perruthenate

TPS

tert-Butyldiphenylsilyl

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Notes

Acknowledgements

Financial support from the Deutsche Forschungsgemeinschaft (Heisenberg-Program) is gratefully acknowledged. MH thanks Prof. D. A. Evans for his hospitality during a stay at Harvard University as a visiting scholar in summer 2003.

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Authors and Affiliations

  1. 1.Institut Für Organische ChemieTechnische Universität DresdenDresdenGermany

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