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Synthesis of illudin S

โœ Scribed by T. Matsumoto; H. Shirahama; A. Ichihara; H. Shin; S. Kagawa; F. Sakan; K. Miyano

Publisher
Elsevier Science
Year
1971
Tongue
French
Weight
189 KB
Volume
12
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

In a previous paper, the total synthesis of dl-llludln M (10) was reported. In this paper we wish to describe synthesis of dl-llludln S dlacetate (Q)2*3'4 through a similar sequence of reactions. Since recon-version of optically active llludln S dlacetate to llludln S by treatment with aqueous sodium carbonate has been performed, the present study represents formally total synthesis of llludln S. 5,6,7 A mixture of cis and tm forms (1 : 3) of the cyclopentenone 1 was obtained In high yield from 2-methyl-2-carbethoxycyolopentanone8 and each stereoisomer was separated by preparative VPC9. The Michael condensation of g-ketosulfoxlde L1 with the trapls comDound& (2 equlv KOBut-ButOH, rt, 2 hr) afforded In 70% yield a single adduct 2, mp 139-140ยฐ; lr (nujol) 1745, 1675, 1230 cm-l; nmr T(CCl,) 9.08 (3H, s, C-CH3), 8.46 (3H, s, 0-C-CH3), 8.00 and

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