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Synfacts 2015; 11(6): 0665-0666
DOI: 10.1055/s-0034-1380860
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

SPS of Seragamide A via Relay-Ring-Closing Metathesis

Contributor(s):
Yasuhiro Uozumi
,
Yoichi M. A. Yamada
,
Takuma Sato
Arndt H.-D, * Rizzo S, Nöcker C, Wakchaure VN, Milroy L.-G, Bieker V, Calderon A, Tran TT. N, Brand S, Dehmelt L, Waldmann H. * Eindhoven University of Technology, The Netherlands; TU Dortmund, Max-Planck-Institut für Molekulare Pflanzenphysiologie, Dortmund and Friedrich-Schiller-Universität, Jena, Germany
Divergent Solid-Phase Synthesis of Natural Product-Inspired Bipartite Cyclodepsipeptides: Total Synthesis of Seragamide A.

Chem. Eur. J. 2015;
21: 5311-5316
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Publication History

Publication Date:
18 May 2015 (online)

 
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Key words

solid-phase synthesis - total synthesis - cyclodepsipeptides - relay-ring-closing metathesis - ruthenium

Significance

The authors present the first total synthesis of seragamide A (isolated from the sponge Suberites japonicus Thiele in 2006) via a solid-phase synthesis–cyclorelease strategy utilizing relay-ring-closing metathesis. Starting from resin (E/Z)-1, the precursor (E/Z)-2 was prepared in seven steps. Relay-ring-closing metathesis of (E/Z)-2 proceeded in the presence of RuCl2(SIMes)(PCy3)(=CHPh) (3) to give (E/Z)-6 in 34% yield based on (E/Z)-1 as a mixture of separable isomers. Treatment of (E)-6 with TFA followed by TBAF provided (E)-7 (seragamide A) in 65% yield (based on the crucial ring-closing step). Similarly, (Z)-6 was converted into (Z)-7 in 59% yield.


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Comment

The present synthetic protocol was also applied to the preparation of a collection of structurally diverse cyclodepsipeptides using various peptides (9 examples) and ketide segments (4 examples).


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