Asymmetric Total Synthesis of Cladosporin and Isocladosporin

The first asymmetric total syntheses of cladosporin and isocladosporin were accomplished in 8 steps with 8% overall yield and 10 steps with 26% overall yield, respectively. The relative configuration of isocladosporin was determined via this total synthesis.

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Bibliographic Details
Published inJournal of organic chemistry Vol. 77; no. 13; pp. 5656 - 5663
Main Authors Zheng, Huaiji, Zhao, Changgui, Fang, Bowen, Jing, Peng, Yang, Juan, Xie, Xingang, She, Xuegong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.07.2012
Amer Chemical Soc
Subjects
antibiotics
chemical reactions
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Isocoumarins - chemical synthesis
Isocoumarins - chemistry
Molecular Structure
Organic chemistry
Physical Sciences
Preparations and properties
research methods
Science & Technology
Stereoisomerism
KETONES
METABOLIC PRODUCTS
PHOSPHORIC-ACID
STEREOSELECTIVE CONSTRUCTION
STEREOCHEMISTRY
MACROLIDE
CIS-2,6-DISUBSTITUTED TETRAHYDROPYRANS
ETHERIFICATION
OXOCARBENIUM IONS
SPIRASTRELLOLIDE
Asymmetric synthesis
Oxygen heterocycle
Relative configuration
Total synthesis
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Summary:The first asymmetric total syntheses of cladosporin and isocladosporin were accomplished in 8 steps with 8% overall yield and 10 steps with 26% overall yield, respectively. The relative configuration of isocladosporin was determined via this total synthesis.
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content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo300805n