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Synfacts 2017; 13(11): 1115
DOI: 10.1055/s-0036-1591428
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Total Synthesis of (±)-Hippolachnin A

Contributor(s):
Erick M. Carreira
,
Philipp Sondermann
Winter N. Trauner D. * Ludwig-Maximilians-Universität München, Germany and New York University, USA
Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (±)-Hippolachnin A.

J. Am. Chem. Soc. 2017;
139: 11706-11709
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Further Information

Publication History

Publication Date:
19 October 2017 (online)

 
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Key words

polyketides - gracilioethers - ylide cycloaddition - hippolachnin A

Significance

Hippolachnin A is a polyketide isolated from a marine sponge showing potent antifungal activity against the opportunistic fungus C. neoformans. The Trauner group reports a concise route to this synthetic target, which is attractive both in terms of bioactivity and a unique molecular scaffold.


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Comment

Known compound A is accessible through a photochemical route. Few synthetic ­manipulations yield D, which undergoes an ylide cycloaddition as a way to install the two exo-positioned ethyl groups. Tin-catalyzed O-alkylation of H followed by desulfation delivers (±)-hippolachnin A.


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