Formal enantioselective synthesis of nhatrangin A

Abstract

A new and straightforward synthesis of the C1–C7 core fragment of nhatrangin A was achieved in 14 steps from achiral 3-hydroxybenzaldehyde, without the need of chiral reagents or enzymatic resolution to introduce the chiral centers.

Gilman reagent toward the synthesis of natural products

“… 94 In continuation of this work, Feuillastre et al reported the enantioselective synthesis of the C1–C7 fragment 206 of nhatrangin A 207 in 2020 ( Scheme 23 ). 95 It was a 14-step sequenced methodology, starting from the easily available achiral 3-hydroxybenzaldehyde, and the overall yield was 13%. The main steps in their scheme were Sharpless asymmetric epoxidation and Gilman reagent-induced regioselective epoxide ring opening reaction.…”

The Asymmetric Total Synthesis and Configuration Confirmation of Aplysiaenal and Nhatrangin A, Truncated Derivatives of Aplysiatoxin and Oscillatoxin

“…Nhatrangin A was also proposed as a biosynthetic intermediate of ATX/OTX due to the structure similarity. To date, three total syntheses and a formal total synthesis of 2 have been reported by Kamal, Yadav, Dias, and Piva, respectively. The NMR spectra reported by Kamal and Yadav were in good agreement with those of the natural product, but did not match those of nhatrangin A as synthesized by Dias, raising questions as to the accuracy of the proposed relative configuration of 2 .…”