Furans as Versatile Synthons: Total Syntheses of Caribenol A and Caribenol B

Hong Dong Hao, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Two complex norditerpenoids, caribenols A and B, were accessed from a common building block. Our synthesis of caribenol A features the diastereoselective formation of the seven-membered ring through a Friedel-Crafts triflation and a late-stage oxidation of a furan ring. The first synthesis of caribenol B was achieved using an intramolecular organocatalytic α-arylation. An unusual intramolecular aldol addition was developed for the assembly of its cyclopentenone moiety, and the challenging trans-diol moiety was installed through a selective nucleophilic addition to a hydroxy 1,2-diketone. Our overall synthetic strategy, which also resulted in a second-generation synthesis of amphilectolide, confirms the usefulness of furans as powerful nucleophiles and versatile synthons.

Original languageEnglish (US)
Pages (from-to)4117-4122
Number of pages6
JournalJournal of the American Chemical Society
Volume139
Issue number11
DOIs
StatePublished - Mar 22 2017

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Furans
Diterpenes
Nucleophiles
Oxidation
caribenol A
amphilectolide
3-hydroxybutanal
furan
cyclopentenone

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Furans as Versatile Synthons : Total Syntheses of Caribenol A and Caribenol B. / Hao, Hong Dong; Trauner, Dirk.

In: Journal of the American Chemical Society, Vol. 139, No. 11, 22.03.2017, p. 4117-4122.

Research output: Contribution to journalArticle

Hao, Hong Dong ; Trauner, Dirk. / Furans as Versatile Synthons : Total Syntheses of Caribenol A and Caribenol B. In: Journal of the American Chemical Society. 2017 ; Vol. 139, No. 11. pp. 4117-4122.
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