Biosynthesis of Providencin: Understanding Photochemical Cyclobutane Formation with Density Functional Theory

Bencan Tang, Robert S. Paton

Research output: Journal PublicationArticlepeer-review

8 Citations (Scopus)
2 Downloads (Pure)

Abstract

The unique structure of furanocembranoid natural product providencin has stimulated biosynthetic hypotheses, especially concerning the formation of its cyclobutanol ring. One such hypothesis involves a photochemically induced Norrish-Yang cyclization in bipinnatin E. We have used computations to assess the feasibility and the stereochemical outcome of this proposed biosynthetic transformation. Density functional theory calculations reveal that the proposed Norrish-Yang cyclization in bipinnatin E is possible and that the stereoselectivity of this step is consistent with that of the natural product.

Original languageEnglish
Pages (from-to)1243-1247
Number of pages5
JournalOrganic Letters
Volume21
Issue number5
DOIs
Publication statusPublished - 1 Mar 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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