Synthetic Approaches to the Axane Family of Sesquiterpenoids. Total Synthesis of dl-Axamide-4, dl-Axisonitrile-4, and (dl)-Axisothiocyanate-4

Balan Chenera, Che Ping Chuang, David J. Hart, Chin Shan Lai

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

Two methods for the preparation of perhydroindan 7 are described. One involves an intramolecular free radical cyclization in a key step and proceeds in 13 steps and 9% yield from anisole (9). The other involves an intramolecular conjugate addition mediated by pyrrolidine (28 → 7) and proceeds in five steps and 30% overall yield from vinylogous ester 29. Two unsuccessful attempts to convert 7 into axane sesquiterpenoids 1–6 are described. The synthesis of axanes 4–6 was achieved using a potassium tert-butoxide catalyzed cyclization of a dienoic keto ester as a key step (47 + 48 → 49). Conversion of α,β-unsaturated ester 49 to vinyl isocyanate 57 was accomplished using a Curtius rearrangement and reduction of 57 with lithium triethylborohydride completed the synthesis of axamide-4 (4). The preparation of axisonitrile-4 (5) and axisothiocyanate-4 (6) from 4 is also described.

Original languageEnglish
Pages (from-to)2018-2029
Number of pages12
JournalJournal of Organic Chemistry
Volume57
Issue number7
DOIs
Publication statusPublished - 1992 Mar 1

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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