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Synthesis of the enantiomers of sclerosporin and sclerosporal to determine the absolute configuration of the natural products

✍ Scribed by Takeshi Kitahara; Tatsuji Matsuoka; Masato Katayama; Shingo Marumo; Kenji Mori

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
221 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

Both the enantiomers of sclerosporin 1 and sclerosporal 2 were synthesized from (-)carvone. (4R, 9R, lOR)-(+)-Sclerosporin and (4R, 9R, lOR)-(-)-sclerosporal were identified as natural enantiomers by bio-assay and by the CD-spectral comparison. Sclerosporin 1, the main sporogenic substance isolated together with sclerosporal 2 by Katayama and Marumo from Sclerotinia fructicola, induced remarkably the formation of asexual arthrospore in the fungal mycelium.' Their structures were proposed as ti-cadalane sesquiterpenes, l_and 2_, which were confirmed by the synthesis of racemates.2 The absolute

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