Strategies and Tactics in Organic Synthesis: Chapter 5. Symmetry-Driven Total Synthesis of Merrilactone A and Resolvin E2

Strategies and Tactics in Organic Synthesis: Chapter 5. Symmetry-Driven Total Synthesis of Merrilactone A and Resolvin E2
ISBN-10
0128056088
ISBN-13
9780128056080
Series
Strategies and Tactics in Organic Synthesis
Category
Science
Pages
344
Language
English
Published
2013-07-29
Publisher
Elsevier Inc. Chapters
Authors
Masayuki Inoue, Daisuke Urabe

Description

In this chapter, we described the asymmetric total synthesis of merrilactone A and resolvin E2 based on the symmetry-driven strategy. The enantio- and diastereoselective transannular aldol reaction of the meso eight-membered diketone led to the efficient total syntheses of both enantiomers of merrilactone A, and the convergent assembly of the pseudo-enantiomeric fragments, prepared through the enantioselective solvolysis of the meso intermediate, resulted in total synthesis of resolvin E2. These syntheses demonstrate the power and generality of the symmetry-driven strategy for construction of both multicyclic and linear natural products.

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