A stereoselective total synthesis of (+/-)-tormesol

作者：Kim Hyoungsu; Bae Hoon; Kim Sanghee; Kim Deukjoon^*; Lee Dongjoo; Paton Robert S

来源：Tetrahedron, 2011, 67(51): 10017-10025.

DOI：10.1016/j.tet.2011.09.022

• Intramolecular ester enolate alkylation
• Tormesol
• Hydroazulene
• Cerium-promoted Grignard reaction

A general strategy for the synthesis of both trans/syn- and trans/anti-sphenolobane diterpenes has been developed, which utilizes an intramolecular ester enolate alkylation (IEEA) as a key step. A stereoselective total synthesis of (+/-)-tormesol (1), an unusual trans/syn-sphenolobane diterpene, was accomplished in 18 steps in 4.1% overall yield from readily available aldehyde 16.

• 出版日期2011-12-23