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A novel approach to a key intermediate in the total synthesis of α-onocerin

✍ Scribed by R.F. Church; R.E. Ireland; J.A. Marshall

Publisher
Elsevier Science
Year
1961
Tongue
French
Weight
242 KB
Volume
2
Category
Article
ISSN
0040-4039

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✦ Synopsis

The total synthesis of the naturally occurring triterpene aonocerin was first accomplished by Stork and co-workers 3 via the Alternate approach to a-onocerin No. 1 6% yield to the acetoxy ester(lO), m.p. 121-122"(C,70.67$; H, 9.33%) by successive treatment with diazomethane, sodium borohydride and then acetic anhydride-pyridine. Ozonization and alkaline hydrolysis of the resulting keto ester., afforded the acid (11) m.p. 185-187" in 51% yield. This acid was identical [mixture m.p., infra-red] to that previously prepared by Stork and co-workers' and thus provides the link between the present work and the previously successful total synthesis of a-onocerin.

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