Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R‑Oxoapratoxin E

In this report, originally proposed apratoxin E (30 S -7), revised apratoxin E (30 R -7), and (30S)/(30R)-oxoapratoxin E (30 S )-38/(30 R )-38 were efficiently prepared by two synthetic methods. The chiral lactone 10, recycled from the degradation of saponin glycosides, was utilized to prepare the k...

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Published inJournal of organic chemistry Vol. 82; no. 20; pp. 10830 - 10845
Main Authors Mao, Zhuo-Ya, Si, Chang-Mei, Liu, Yi-Wen, Dong, Han-Qing, Wei, Bang-Guo, Lin, Guo-Qiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.10.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Depsipeptides - chemical synthesis
Depsipeptides - chemistry
Molecular Structure
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
POTENT
ASYMMETRIC-SYNTHESIS
RING-CLOSING METATHESIS
HOIAMIDE
CYTOTOXIC CYCLIC DEPSIPEPTIDES
OLEFIN METATHESIS
STEREOSELECTIVE-SYNTHESIS
CYCLODEPSIPEPTIDES
MARINE NATURAL-PRODUCTS
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Summary:In this report, originally proposed apratoxin E (30 S -7), revised apratoxin E (30 R -7), and (30S)/(30R)-oxoapratoxin E (30 S )-38/(30 R )-38 were efficiently prepared by two synthetic methods. The chiral lactone 10, recycled from the degradation of saponin glycosides, was utilized to prepare the key nonpeptide fragment 9. Our alternative convergent assembly strategy was applied to the divergent synthesis of revised apratoxin E and its three analogues. Moreover, ring-closing metathesis (RCM) was for the first time found to be an efficient strategy for the macrocyclization of apratoxins.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b01598