Enantioselective synthesis of the ABC ring motif of norzoanthamine based on asymmetric robinson annulation reactions

Thong X. Nguyen, Marianna Dakanali, Lynnie Trzoss, Emmanuel A. Theodorakis

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

An enantioselective strategy for the synthesis of tetracyclic motif 5, representing the northern fragment of norzoanthamine, is presented. Key to the strategy is the use of two asymmetric Robinson annulation reactions that produce the tricyclic ABC ring system with excellent stereoselectivity. Further functionalization at the periphery of the C ring produces compound 5 containing six contiguous stereocenters of the natural product.

Original languageEnglish (US)
Pages (from-to)3308-3311
Number of pages4
JournalOrganic Letters
Volume13
Issue number13
DOIs
StatePublished - Jul 1 2011

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Stereoselectivity
Biological Products
rings
synthesis
fragments
products
norzoanthamine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Enantioselective synthesis of the ABC ring motif of norzoanthamine based on asymmetric robinson annulation reactions. / Nguyen, Thong X.; Dakanali, Marianna; Trzoss, Lynnie; Theodorakis, Emmanuel A.

In: Organic Letters, Vol. 13, No. 13, 01.07.2011, p. 3308-3311.

Research output: Contribution to journalArticle

Nguyen, Thong X. ; Dakanali, Marianna ; Trzoss, Lynnie ; Theodorakis, Emmanuel A. / Enantioselective synthesis of the ABC ring motif of norzoanthamine based on asymmetric robinson annulation reactions. In: Organic Letters. 2011 ; Vol. 13, No. 13. pp. 3308-3311.
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