Total synthesis of berkelic acid

TN Snaddon, P Buchgraber, S Schulthoff…

Index: Snaddon, Thomas N.; Buchgraber, Philipp; Schulthoff, Saskia; Wirtz, Conny; Mynott, Richard; Fuerstner, Alois Chemistry - A European Journal, 2010 , vol. 16, # 40 p. 12133 - 12140

Full Text: HTML

Citation Number: 38

Abstract

Abstract A productive total synthesis of both enantiomers of berkelic acid (1) is outlined that takes the structure revision of this bioactive fungal metabolite previously proposed by our group into account. The successful route relies on a fully optimized triple-deprotection/1, 4- addition/spiroacetalization cascade reaction sequence, which delivers the tetracyclic core 32 of the target as a single isomer in excellent yield. The required cyclization precursor 31 ...

Related Articles:

Introduction of the (−)-Berkelic Acid Side Chain and Assignment of the C-22 Stereochemistry

[Wu, Xiaoxing; Zhou, Jingye; Snider, Barry B. Journal of Organic Chemistry, 2009 , vol. 74, # 16 p. 6245 - 6252]

Scalable Total Synthesis of (−)??Berkelic Acid by Using a Protecting??Group??Free Strategy

[Fananas, Francisco J.; Mendoza, Abraham; Arto, Tamara; Temelli, Baris; Rodriguez, Felix Angewandte Chemie - International Edition, 2012 , vol. 51, # 20 p. 4930 - 4933]

Scalable Total Synthesis of (−)??Berkelic Acid by Using a Protecting??Group??Free Strategy

[Fananas, Francisco J.; Mendoza, Abraham; Arto, Tamara; Temelli, Baris; Rodriguez, Felix Angewandte Chemie - International Edition, 2012 , vol. 51, # 20 p. 4930 - 4933]

More Articles...