Total Synthesis of Asperphenins A and B

The first total synthesis of asperphenins A and B has been accomplished in a concise, highly stereoselective fashion from commercially available materials (15 steps, 9.7% and 14.2% overall yields, respectively). The convergent route featured the judicious choice of protecting groups, fragment assemb...

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Published inOrganic letters Vol. 20; no. 19; pp. 6170 - 6173
Main Authors Yan, Jia-Lei, Cheng, Yingying, Chen, Jing, Ratnayake, Ranjala, Dang, Long H, Luesch, Hendrik, Guo, Yian, Ye, Tao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.10.2018
Amer Chemical Soc
Subjects
Alkenes - chemistry
Amides - chemical synthesis
Amines - chemical synthesis
Aspergillus - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cycloaddition Reaction
Ketones - chemical synthesis
Molecular Structure
Oxidation-Reduction
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
KETONES
ASYMMETRIC-SYNTHESIS
REAGENTS
ACID
ANALOGS
AMIDE
STEREOCHEMICAL ASSIGNMENT
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Summary:The first total synthesis of asperphenins A and B has been accomplished in a concise, highly stereoselective fashion from commercially available materials (15 steps, 9.7% and 14.2% overall yields, respectively). The convergent route featured the judicious choice of protecting groups, fragment assembly strategy and a late-stage iron-catalyzed Wacker-type selective oxidation of an internal alkene to the corresponding ketone.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02652