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. 2020 May 4;59(19):7444-7449.
doi: 10.1002/anie.202001350. Epub 2020 Mar 17.

Total Synthesis of Farnesin through an Excited-State Nazarov Reaction

Yonglei Que  1 , Hao Shao  1 , Haibing He  2 , Shuanhu Gao  1   2
Affiliations

Total Synthesis of Farnesin through an Excited-State Nazarov Reaction

Yonglei Que et al. Angew Chem Int Ed Engl. .

Abstract

The asymmetric total synthesis of farnesin, a rearranged ent-kaurenoid, was achieved through a convergent approach involving photo-Nazarov and intramolecular aldol cyclizations to build the syn-syn-syn hydrofluorenol ABC ring system and bicyclo[3.2.1]octane CD ring system in the first application of a UV-light-induced excited-state Nazarov cyclization of a non-aromatic dicyclic divinyl ketone in a total synthesis. Unlike the conventional acid-promoted ground-state Nazarov reaction, the excited-state Nazarov reaction enables stereospecific formation of the highly strained syn-syn-syn-fused hydrofluorenone scaffold through a disrotatory cyclization.

Keywords: Nazarov cyclization; polycycles; strained molecules; terpenoids; total synthesis.

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References

    1. None
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    1. For reviews of synthetic studies of ent-kaurenoids, see:

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