[3 + 2] annulation of allylic silanes in acyclic stereocontrol: Total synthesis of (9S)-dihydroerythronolide A

Zhi H. Peng, Keith Woerpel

Research output: Contribution to journalArticle

Abstract

The [3 + 2] annulation reactions of allylic silanes can be utilized to achieve acyclic stereocontrol. This method was employed as a key step in an enantioselective total synthesis of (9S)-dihydroerythronolide A. The key annulation reaction served to establish most of the stereochemistry of the target, including the two tetrasubstituted carbon stereocenters. The symmetry of the target molecule allowed it to be disconnected into two equally sized fragments, both of which were generated from the same annulation reaction. The two fragments were coupled using a tin(II)-mediated chelation-controlled aldol reaction of an ∞-benzyloxy ethyl ketone. This convergent total synthesis of (9S)-dihydroerythronolide A was accomplished with the longest linear sequence of 29 steps and in 5.4% overall yield.

Original languageEnglish (US)
Pages (from-to)6018-6019
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number20
DOIs
StatePublished - May 21 2003

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Silanes
Stereochemistry
Tin
Chelation
Ketones
Carbon
Molecules
erythronolide A
3-hydroxybutanal

ASJC Scopus subject areas

  • Chemistry(all)

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[3 + 2] annulation of allylic silanes in acyclic stereocontrol : Total synthesis of (9S)-dihydroerythronolide A. / Peng, Zhi H.; Woerpel, Keith.

In: Journal of the American Chemical Society, Vol. 125, No. 20, 21.05.2003, p. 6018-6019.

Research output: Contribution to journalArticle

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