Studies on Total Synthesis of the Olivomycins

Robert P. Hatch, Jayant Shringarpure, Steven M. Weinreb

Research output: Contribution to journalArticle

103 Citations (Scopus)

Abstract

Studies directed toward total synthesis of olivin (4), the aglycon of the olivomycin antitumor antibiotics, are described. The key aldehyde 23, containing the tricyclic nucleus of olivin, has been prepared in 14 steps from 3,5-di-methoxybenzyl chloride. Methods for construction of the olivin hydroxy ketone side chain were also investigated. Attempted addition of trianion 24 to simple aldehydes was unsuccessful. Cyclohexanecarboxaldehyde, a model for aldehyde 23, was converted to dithiane 36, which in two steps was transformed to ketone 38. Hydroxylation of 38 with m-CPBA via a kinetic enolate and trimethylsilyl ether 39 produced a single acyloin, having either structure 40 or 42.

Original languageEnglish (US)
Pages (from-to)4172-4177
Number of pages6
JournalJournal of Organic Chemistry
Volume43
Issue number21
DOIs
StatePublished - Jan 1 1978

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Olivomycins
Aldehydes
Ketones
Hydroxylation
Ether
Chlorides
Anti-Bacterial Agents
Kinetics
olivin

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Hatch, R. P., Shringarpure, J., & Weinreb, S. M. (1978). Studies on Total Synthesis of the Olivomycins. Journal of Organic Chemistry, 43(21), 4172-4177. https://doi.org/10.1021/jo00415a041
Hatch, Robert P. ; Shringarpure, Jayant ; Weinreb, Steven M. / Studies on Total Synthesis of the Olivomycins. In: Journal of Organic Chemistry. 1978 ; Vol. 43, No. 21. pp. 4172-4177.
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Hatch, RP, Shringarpure, J & Weinreb, SM 1978, 'Studies on Total Synthesis of the Olivomycins', Journal of Organic Chemistry, vol. 43, no. 21, pp. 4172-4177. https://doi.org/10.1021/jo00415a041

Studies on Total Synthesis of the Olivomycins. / Hatch, Robert P.; Shringarpure, Jayant; Weinreb, Steven M.

In: Journal of Organic Chemistry, Vol. 43, No. 21, 01.01.1978, p. 4172-4177.

Research output: Contribution to journalArticle

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