Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Stereoselective Synthesis of Unnatural Stereoisomers of LL-P880β and LL-P880γ, Pestalotin Analogues from Penicillium sp.
Mitsunori KIRIHATAMasayuki OHEItsuo ICHIMOTOHiroo UEDA
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1992 年 56 巻 11 号 p. 1825-1828

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A synthesis of unnatural stereoisomers of LL-P880β (2) and subsequent transformation of 2 into LL-P880γ (3) were achieved by starting from diacetoneglucose (4). A chiral building block, 5-deoxy-α-D-ribofuranose derivative 9, was derived from 4 by two synthetic routes. A chiral aldehyde (20) was prepared through a six-step sequence from 9, and treated with the dianion of methyl acetoacetate to complete the synthesis of (6S, 1'R, 2'R)-LL-P880β (2a) and its C6-epimer (2b). After converting 2a to its diacetate (23), this was transformed into (1'R, 2'R)-LL-P880γ (3a) via a 5-bromopyran derivative (24).
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