Synthetic Approach to Cytochalasins

Moohi Yoo Kim, John E. Starrett, Steven M. Weinreb

Research output: Contribution to journalArticle

62 Citations (Scopus)

Abstract

Studies directed toward total synthesis of cytochalasin B (1) and A (2) are described. A simple acyclic unit, 12, intended for incorporation into the macrolactone ring of the cytochalasins has been prepared in seven steps from citronellol (5). The isoindolone nucleus 36 has been prepared by a Diels-Alder strategy via adduct 31. Conversion of this adduct to methoxy lactam 33 and coupling with tribenzylaluminum afforded lactam 34. Hydroxylation of the enolate of 34 gave isoindolone 35 containing the five chiral centers necessary for preparation of 1 and 2. Debenzylation of 35 produced diol 36, which will be combined with fragment 12 to ultimately complete a cytochalasin total synthesis.

Original languageEnglish (US)
Pages (from-to)5383-5389
Number of pages7
JournalJournal of Organic Chemistry
Volume46
Issue number26
DOIs
StatePublished - Jan 1 1981

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Cytochalasins
Lactams
Hydroxylation
Cytochalasin B
Isoindol-1-one
citronellol

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Kim, M. Y., Starrett, J. E., & Weinreb, S. M. (1981). Synthetic Approach to Cytochalasins. Journal of Organic Chemistry, 46(26), 5383-5389. https://doi.org/10.1021/jo00339a027
Kim, Moohi Yoo ; Starrett, John E. ; Weinreb, Steven M. / Synthetic Approach to Cytochalasins. In: Journal of Organic Chemistry. 1981 ; Vol. 46, No. 26. pp. 5383-5389.
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Kim, MY, Starrett, JE & Weinreb, SM 1981, 'Synthetic Approach to Cytochalasins', Journal of Organic Chemistry, vol. 46, no. 26, pp. 5383-5389. https://doi.org/10.1021/jo00339a027

Synthetic Approach to Cytochalasins. / Kim, Moohi Yoo; Starrett, John E.; Weinreb, Steven M.

In: Journal of Organic Chemistry, Vol. 46, No. 26, 01.01.1981, p. 5383-5389.

Research output: Contribution to journalArticle

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AB - Studies directed toward total synthesis of cytochalasin B (1) and A (2) are described. A simple acyclic unit, 12, intended for incorporation into the macrolactone ring of the cytochalasins has been prepared in seven steps from citronellol (5). The isoindolone nucleus 36 has been prepared by a Diels-Alder strategy via adduct 31. Conversion of this adduct to methoxy lactam 33 and coupling with tribenzylaluminum afforded lactam 34. Hydroxylation of the enolate of 34 gave isoindolone 35 containing the five chiral centers necessary for preparation of 1 and 2. Debenzylation of 35 produced diol 36, which will be combined with fragment 12 to ultimately complete a cytochalasin total synthesis.

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Kim MY, Starrett JE, Weinreb SM. Synthetic Approach to Cytochalasins. Journal of Organic Chemistry. 1981 Jan 1;46(26):5383-5389. https://doi.org/10.1021/jo00339a027