Advances in the Total Synthesis of Cyclodepsipeptide (+)-Jasplakinolide (Jaspamide) and its Analogs

Author(s): Yuan-Yuan Xu, Chao Liu, Zhao-Peng Liu

Journal Name: Current Organic Synthesis

Volume 10 , Issue 1 , 2013


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Abstract:

(+)-Jasplakinolide (jaspamide) is a 19-membered depsipeptide identified from the marine sponge in 1986. It features with a macrolactam joined by a tripeptide unit and a non-peptide polypropionate sector containing three chiral centers. Along with the common acid L-alanine, jasplakinolide contains an unnatural D-amino acid 2-bromoabrine and the rare (R)-β-tyrosine. The unique and complex structure, as well as the remarkable biological properties of (+)-jasplakinolide, has inspired the continuous efforts in the total synthesis of jasplakinolide and its analogs. Most of the total syntheses are achieved based on the macrolactonization-centered strategies. Another novel approach is highlighted by an efficient solid phase-based preparation of the linear peptide chain followed by ruthenium-catalyzed ring closing metathesis of the macrocycle. This review will summarize the achievements in the total synthesis of (+)-jasplakinolides, including the synthetic methods for the important intermediates (2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoic acid, (R)-2- bromoabrine, (R)-β-tyrosine and their related derivatives.

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Article Details

VOLUME: 10
ISSUE: 1
Year: 2013
Page: [67 - 89]
Pages: 23
DOI: 10.2174/1570179411310010004
Price: $65

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