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Total Synthesis of (+)-Nivetetracyclate A. | LitMetric

Total Synthesis of (+)-Nivetetracyclate A.

Org Lett

Fachbereich Chemie , Philipps- Universität Marburg, Hans-Meerwein-Strasse 4 , D-35043 Marburg , Germany.

Published: February 2019

A stereoselective synthetic approach to the natural product (+)-nivetetracyclate A is reported. The tetracyclic skeleton was assembled in a convergent manner by an alkylation to a diarylmethane and subsequent Friedel-Crafts acylation. Further key steps are an asymmetric Sharpless epoxidation and the boron trifluoride-mediated diastereoselective rearrangement of an epoxy alcohol to a β-hydroxy aldehyde. Optimized timing for the deprotection step and the chemo- and stereoselective Noyori -transfer hydrogenation of a 1,4-diketone allowed the late stage introduction of the C4 stereocenter.

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Source
http://dx.doi.org/10.1021/acs.orglett.8b04044DOI Listing

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