Synthesis of Clerodane Diterpenoids and Related Compounds - Stereoselective Construction of the Decalin Skeleton with Multiple Contiguous Stereogenic Centers

Takashi Tokoroyama

doi:10.1055/s-2000-6381

Synthesis 2000; 2000(5): 611-633
DOI: 10.1055/s-2000-6381

review

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Synthesis of Clerodane Diterpenoids and Related Compounds - Stereoselective Construction of the Decalin Skeleton with Multiple Contiguous Stereogenic Centers

Takashi Tokoroyama^*

^*3-25-1 Makizuka-dai, Sakai-shi, Osaka 590-0114, Japan; Fax + 81(722)93 23 03; E-mail: toko-tak@wc4.so-net.ne.jp

Abstract

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Stereoselective construction of contiguous stereogenic centers in the decalin ring - usually four - is central to the synthesis of clerodane diterpenoids and the present review surveys the methods utilized to meet this task. Major strategies for the stereocontrol are: (i) diastereoface-selective reactions on a rigid ring, (ii) conformational preference of a rigid ring structure in an equilibrium condition, and (iii) diastereoselective cyclization. According to the classification based on the methods for construction of the stereogenic centers, an overview will be presented to various synthetic studies on clerodane and related natural products, which are of current interest in view of biological activity.

clerodane diterpenoids - bioactive natural products - stereoselective synthesis - diastereoface selection on rigid ring - diastereoselective cyclizations

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