Total synthesis of sandresolide B and amphilectolide

Ingrid T. Chen, Irina Baitinger, Lucas Schreyer, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

The total synthesis of the diterpenoids sandresolide B and amphilectolide from a common furan building block is presented. Key steps include palladium-mediated carbonylation, lanthanide catalyzed ring closure, Myers alkylation, intramolecular Friedel-Crafts acylation, photooxygenation, and a Kornblum-DeLaMare rearrangement.

Original languageEnglish (US)
Pages (from-to)166-169
Number of pages4
JournalOrganic Letters
Volume16
Issue number1
DOIs
StatePublished - Jan 3 2014

Fingerprint

Carbonylation
acylation
Acylation
Lanthanoid Series Elements
Diterpenes
furans
alkylation
Alkylation
Palladium
closures
palladium
vehicles
rings
synthesis
furan
sandresolide B
amphilectolide
ent-7beta,14-dihydroxy-11alpha-methoxy-18-aldehyde-11beta-20-epoxy-kaur-16-en-15-one

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Chen, I. T., Baitinger, I., Schreyer, L., & Trauner, D. (2014). Total synthesis of sandresolide B and amphilectolide. Organic Letters, 16(1), 166-169. https://doi.org/10.1021/ol403156r

Total synthesis of sandresolide B and amphilectolide. / Chen, Ingrid T.; Baitinger, Irina; Schreyer, Lucas; Trauner, Dirk.

In: Organic Letters, Vol. 16, No. 1, 03.01.2014, p. 166-169.

Research output: Contribution to journalArticle

Chen, IT, Baitinger, I, Schreyer, L & Trauner, D 2014, 'Total synthesis of sandresolide B and amphilectolide', Organic Letters, vol. 16, no. 1, pp. 166-169. https://doi.org/10.1021/ol403156r
Chen IT, Baitinger I, Schreyer L, Trauner D. Total synthesis of sandresolide B and amphilectolide. Organic Letters. 2014 Jan 3;16(1):166-169. https://doi.org/10.1021/ol403156r
Chen, Ingrid T. ; Baitinger, Irina ; Schreyer, Lucas ; Trauner, Dirk. / Total synthesis of sandresolide B and amphilectolide. In: Organic Letters. 2014 ; Vol. 16, No. 1. pp. 166-169.
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