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Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products

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Abstract

A divergent and expeditious access to haterumadienone- and puupehenone-type marine natural products has been achieved by using a newly developed hemiacetalization/dehydroxylation/hydroxylation/retro-hemiacetalization tandem reaction as one of the key steps. Its applicability is showcased by the first synthesis of haterumadienone, 20-hydroxyhaterumadienone, 20-epihydroxy-haterumadienone and 20-acetoxy-haterumadienone, as well as the facile synthesis of puupehenone, puupehedione and puupehenol. The synthesis is efficient, and atom- and step-economical (6 to 9 steps from commercially available starting materials), and requires no protecting groups and transition metals.

Graphical abstract: Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products

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Publication details

The article was received on 07 Mar 2017, accepted on 19 Apr 2017 and first published on 19 Apr 2017


Article type: Communication
DOI: 10.1039/C7GC00704C
Citation: Green Chem., 2017, Advance Article
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    Protecting-group-free synthesis of haterumadienone- and puupehenone-type marine natural products

    H. Wang, H. Li, J. Wang and Y. Wu, Green Chem., 2017, Advance Article , DOI: 10.1039/C7GC00704C

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