Tetrahedron

Total synthesis of seco-lateriflorone

EJ Tisdale, BG Vong, H Li, SH Kim, C Chowdhury…

Index: Tisdale, Eric J.; Vong, Binh G.; Li, Hongmei; Kim, Sun Hee; Chowdhury, Chinmay; Theodorakis, Emmanuel A. Tetrahedron, 2003 , vol. 59, # 35 p. 6873 - 6887

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Citation Number: 62

Abstract

A convergent strategy toward the synthesis of lateriflorone (5) is described. Our approach is based on biosynthetic considerations and draws on a sequence of prenylation, oxygenation and Claisen reactions for the construction of chromenequinone 6, and a tandem Claisen/Diels–Alder reaction cascade for the synthesis of caged tricycle 7. Union of fragments 6 and 7 led to the synthesis of seco-lateriflorone (49).