ArticleChemistry (Weinheim an der Bergstrasse, Germany)2010
Total synthesis and configurational assignment of chondramide A.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Synthesis of the polyketide section of seragamide A and related cyclodepsipeptides via Negishi cross coupling.Beilstein journal of organic chemistry · 2019Article
- Modulation of actin dynamics as potential macrophage subtype-targeting anti-tumour strategy.Scientific reports · 2017Article
- Synthetic chondramide A analogues stabilize filamentous actin and block invasion by Toxoplasma gondii.Journal of natural products · 2013Article
- Synthesis of chondramide A analogues with modified β-tyrosine and their biological evaluation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2011Article
- Biostructural features of additional jasplakinolide (jaspamide) analogues.Journal of natural products · 2011Article
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Authors and funding
3 authors.
Funding
Abstract
The first total synthesis of the cyclodepsipeptide chondramide A (2 b) is described. This depsipeptide is composed of four subunits, namely L-alanine, N-Me-D-tryptophan, 3-amino-2-methoxy-propionic acid (beta-tyrosine derivative), and a 7-hydroxy-alkenoic acid. While the configuration of the stereogenic centers in the 7-hydroxy-alkenoic acid were known, the configuration of the tyrosine derivative required clarification and turned out to be (2S,3R) or (2L,3L), respectively. The synthesis of the 3-amino-2-methoxy-3-arylpropanoic ester 20 b relied on an asymmetric dihydroxylation yielding diol ent-15 a followed by a regioselective Mitsunobu substitution leading to 3-azido-2-hydroxypropanoate 18 b. We could also show that the ester bond in the seco compound 26 b can be fashioned by a Mitsunobu esterification by using hydroxy ester (7S)-7 and the tripeptide acid 25 b. This synthesis should allow for the preparation of various analogues.
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