A Stereospecific Total Synthesis of α-Santalol

E. J. Corey, H. A. Kirst, John A. Katzenellenbogen

Research output: Contribution to journalArticlepeer-review

Abstract

A stereospecific synthetic route to the important constituent of sandalwood oil, α-santalol, from the readily accessible (–)-π-bromotricyclene is outlined. The synthesis illustrates a number of new synthetic methods including (1) chain extension using 3-trimethylsilylpropargyllithium, (2) stereo- and position-specific addition of diisobutylaluminum hydride to the lithium salt of a propargylic alcohol, and (3) stereospecific methoxycarbonylation of a vinylic iodide by nickel carbonyl and sodium methoxide in methanol. The scope of the synthesis as a general route to the structural olefinic unit RCH2CH=C(CH3)CH2OH in which H and CH3 are cis is further illustrated by the case R = n-C6H13.

Original languageEnglish (US)
Pages (from-to)6314-6320
Number of pages7
JournalJournal of the American Chemical Society
Volume92
Issue number21
DOIs
StatePublished - Oct 1 1970
Externally publishedYes

ASJC Scopus subject areas

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

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