Toward the Total Synthesis of (±)-Andrastin C

An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels–Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 1; pp. 93 - 103
Main Authors Okamoto, Rei, Takeda, Kazutaka, Tokuyama, Hidetoshi, Ihara, Masataka, Toyota, Masahiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.01.2013
Amer Chemical Soc
Subjects
Androstadienes - chemical synthesis
Androstadienes - chemistry
Chemistry
Chemistry, Organic
Molecular Structure
Phenanthrenes - chemical synthesis
Phenanthrenes - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
MITSUNOBU REACTION
PINGUISANE-TYPE SESQUITERPENOIDS
PALLADIUM-CATALYZED CYCLOALKENYLATION
(+/-)-METHYL GUMMIFEROLATE
RADICAL CYCLIZATION
1ST TOTAL-SYNTHESIS
FORMAL TOTAL-SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
PROTEIN FARNESYLTRANSFERASE INHIBITORS
ENANTIOSPECIFIC APPROACH
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Summary:An efficient approach to generate a fully functionalized cyclopenta[a]phenanthrene 34, the basic carbon framework of andrastin C (1c), is described. The present synthetic route features a stereoselective intramolecular Diels–Alder reaction of triene 12 and an intramolecular carbonyl ene reaction of 3-phenanthrenyl-2-(methoxymethoxy)propanal 31.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo301948h