A facile approach for the total synthesis of neurotrophic diyne tetraol petrosiol A and petrosiol E

摘要

The first total synthesis of neurotrophic diacetylenic tetraol, petrosiol A and stereoselective total synthesis of petrosiol E was accomplished. The total synthesis involves Cadiot-Chodkiewicz coupling reaction as the key step for petrosiol A. The diastereorich chiral alcohol (third chiral center) was synthesized from CBS mediated stereoselective ketone reduction reaction for petrosiol E. Of the three chiral centers, the two chiral centers are originated from (+)-diethyl L-tartrate and the third chiral center was generated by an addition reaction of lithium trimethylsilylacetylide leading to two diastereomers which were used for the synthesis of both the natural products and their diastereomer C6-epi-petrosiol A and C6-epi-petrosiol E, respectively. (C) 2016 Elsevier Ltd. All rights reserved.