Proof of the (<i>S,S</i>) Configuration of (−)‐Bissetone by Synthesis from <scp>D</scp>‐Glucose

Abstract

(S,S)-Bissetone 1, 2 constituent cf the gorgonian soft coral Briareum polyanthes, can be synthesized in eight steps from D-glucose (overall yield 37%). The central intermediate is the dihydropyranone 2, whose six-step synthesis from D-glucose involving two one-pot reactions has been vastly improved and is now possible on a l00g scale. The conversion of 2 into 1 can be achieved in two ways.