Construction of the Myrioneuron alkaloids

A total synthesis of (±)-Myrioneurinol

Anthony J. Nocket, Yiqing Feng, Steven M. Weinreb

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A strategy has been developed that culminated in a stereoselective total synthesis of the tetracyclic antimalarial Myrioneuron alkaloid myrioneurinol. The synthesis relies on three highly diastereoselective reactions, including an intramolecular chelation-controlled Michael spirocyclization of an N-Cbz-lactam titanium enolate to an α,β-unsaturated ester for construction of the A/D-ring system and the attendant C5 (quaternary), C6 relative stereochemistry; a malonate enolate conjugate addition to a nitrosoalkene in order to install the appropriate functionality and establish the configuration at C7; and an intramolecular aza-Sakurai reaction to form the B-ring and the accompanying C9 and C10 stereocenters.

Original languageEnglish (US)
Pages (from-to)1116-1129
Number of pages14
JournalJournal of Organic Chemistry
Volume80
Issue number2
DOIs
StatePublished - Jan 16 2015

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Alkaloids
Lactams
Stereochemistry
Antimalarials
Chelation
Titanium
Esters
myrioneurinol
malonic acid

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Nocket, Anthony J. ; Feng, Yiqing ; Weinreb, Steven M. / Construction of the Myrioneuron alkaloids : A total synthesis of (±)-Myrioneurinol. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 2. pp. 1116-1129.
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Construction of the Myrioneuron alkaloids : A total synthesis of (±)-Myrioneurinol. / Nocket, Anthony J.; Feng, Yiqing; Weinreb, Steven M.

In: Journal of Organic Chemistry, Vol. 80, No. 2, 16.01.2015, p. 1116-1129.

Research output: Contribution to journalArticle

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