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.
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
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