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Studies of a Diazo Cyclopropanation Strategy for the Total Synthesis of (−)-Lundurine A by Hong-Xiu Huang; Shuai-Jiang Jin; Jin Gong; Dan Zhang; Hao Song; Yong Qin is a Chemistry article available to read on EtoBox.

What is Studies of a Diazo Cyclopropanation Strategy for the Total Synthesis of (−)-Lundurine A about?

The bioactive Kopsia alkaloids lundurines A-D are the only natural products known to contain indolylcyclopropane. Achieving their syntheses can provide important insights into their biogenesis, as well as novel synthetic routes for complex natural products. Asymmetric total synthesis of (-)-lundurine A has previously been achieved through a Simmons-Smith cyclopropanation strategy. Here, the total synthesis of (-)-lundurine A was carried out using a metal-catalyzed diazo cyclopropanation strategy. In order to avoid a carbene CH insertion side reaction during cyclopropanation of α-diazo- carboxylates or cyanides, a one-pot, copper-catalyzed Bamford-Stevens diazotization/diazo decomposition/cyclopropanation cascade was developed, involving hydrazone. This approach simultaneously generates the C/D/E ring system and the two chiral quaternary centers at C2 and C7.

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Author

Hong-Xiu Huang; Shuai-Jiang Jin; Jin Gong; Dan Zhang; Hao Song; Yong Qin

Publisher

Wiley

Published

2015

Language

EN

Field

Chemistry (Physical Sciences)