Practical synthesis of aromatic bisabolanes: Synthesis of 1,3,5-bisabolatrien-7-ol, peniciaculin A and B, and hydroxysydonic acid

The enantioselective synthesis of aromatic bisabolanes, such as 1,3,5-bisabolatrien-7-ol, peniciaculin A and B, and hydroxysydonic acid, has been described. Our methodology for the total synthesis of aromatic bisabolanes involves the stereoselective construction of the C-7 stereogenic center via a Sharpless asymmetric dihydroxylation reaction, followed by a SmI2-mediated Julia olefination. Preliminary results obtained for the odor evaluation of 1,3,5-bisabolatrien-7-ol and the confirmation of the absolute configurations of peniciaculin A and B are also described. (C) 2021 Elsevier Ltd. All rights reserved.