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Issue 30, 2019
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Total synthesis of (+)-ar-macrocarpene

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Abstract

This report features the first catalytic asymmetric total synthesis of a sesquiterpene, (+)-ar-macrocarpene (1), in 7 steps with 42.1% overall yields from commercially available inexpensive 5,5-dimethylcyclohexane 1,3-dione. This strategy relies on a key [3,3]-sigmatropic rearrangement effecting reductive transposition through allylic diazene rearrangement (ADR) in a single step from intermediate allylic alcohol (+)-12 under the Mitsunobu reaction conditions with o-nitrobenzenesulfonyl hydrazide (o-NBSH). Enantioselective reduction of α-bromo vinylogous ester 16 under the Corey–Bakshi–Shibata reduction conditions forges the required stereocenter in the allylic alcohol (+)-12 in a highly enantioenriched manner (95% ee).

Graphical abstract: Total synthesis of (+)-ar-macrocarpene

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Publication details

The article was received on 18 Jun 2019, accepted on 09 Jul 2019 and first published on 09 Jul 2019


Article type: Communication
DOI: 10.1039/C9OB01373C
Org. Biomol. Chem., 2019,17, 7140-7143

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    Total synthesis of (+)-ar-macrocarpene

    A. Khatua, S. Niyogi and V. Bisai, Org. Biomol. Chem., 2019, 17, 7140
    DOI: 10.1039/C9OB01373C

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