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A stereoselective osmylation approach to polyoxygenated natural products. Synthesis of C(1)-C(7) and C(7)-C(13) subunits of erythronolide A

✍ Scribed by Gyu Kim Young; Whang Konghyun; R.J. Cooke; Jin K. Cha

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 284 KB
Volume: 31
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)89042-5

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✦ Synopsis

The key synthons 2 and 3 [with suitable protecting groups] of the erythronolide A seco acid (1) have been prepared in an enantiomerically pure form, utilizing a stereoselective osmylation of chiral hydroxy (Z,E)-diene ester 6a and subsequent hydrogenation. Recent interest in macrolide and ionophore antibiotics has stimulated the development of efficient methods for the stereocontrolled synthesis of densely functionalized acyclic or tetrahydrofuran or -pyran molecules [e.g., erythronolide A seco acid (l)].l-3 As a part of our research objectives directed at the total synthesis of these polyoxygenated natural products (Scheme I), we previously reported an efficient, enantio-and stereoselective preparation of a

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