61 微生物還元を活用する光学活性テルペノイドの合成(ポスター発表の部)

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In order to develope a method to convert an isolated double bond in acyclic isoprenoids into chiral epoxide, α-hydroxy ketone was reduced with baker's yeast resulting in the formation of (R)-diol in high enantiomeric purity. The diols thus obtained could be converted easily into various isoprenoids having (S)-epoxide (Table). From (R)-diol 3 derived from geraniol, the segments such as 8 and 9 for the synthesis of eurylene (1) were readily prepared. The left-half segment for the synthesis of quassiol A (2) was also synthesized from the diol 10 derived from farnesol (scheme 1). The microbial reduction was then applied to the synthesis of haplomitrenone (12) isolated from the liverworts, Haplomitrium mnioides, and compound 22 close to 12 was synthesized through the diol 17 obtained by yeast reduction (Scheme 2). Finally, the synthesis of both enantiomers of sarcophytols A (23) and T (26) isolated from the Sarcophyton species of soft coral was accomplished (scheme 4). The diol 34 obtained by yeast reduction of 33 was converted into the ethers (+)-37 and (-)-38. [2,3]Wittig rearrangement of (+)-37 proceeded stereospecifically to yield natural-type sarcophytol A [(S)-23], while (-)-38 afforded unnatural-type sarcophytol T [(R)-26] by reverse chirality transfer in high yield. The diol 34 was then converted through the epoxide 39 into the ethers (-)-37 and (+)-38, from which unnatural-type (R)-23 and natural-type (S)-26 were synthesized by the similar stereospecific [2,3]Wittig rearrangement. On the basis of molecular mechanics calculations, the conformations of the transition state of the stereospecific [2,3]Wittig rearrangement were discussed.
天然有機化合物討論会の論文
1993-09-10

61 微生物還元を活用する光学活性テルペノイドの合成(ポスター発表の部)

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