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Total synthesis of tetracyclic triterpenes 2 an efficient synthesis of 1,4-dimethoxy-14α-methyl-11-oxoestra-1,3,5(10)-triene

✍ Scribed by Balan Chenera; Usha Venkitachalam; Donald Ward; William Reusch

Book ID: 104204464
Publisher: Elsevier Science
Year: 1986
Tongue: French
Weight: 803 KB
Volume: 42
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)87311-7

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✦ Synopsis

Diels-Alder cycloaddition OP 1,4-benzcquinone with diene 2 gave the a-endo adduct 6 in good yield. Acid catalyzed aromatization of 6 was unconjugated hydroquinone derivative 7 or controllegclgg ;;omi; ;tveThzi;;;:thh; the conjugated A derivative 12 gave acid-labile epoxides 17 and 18, respectively on the strength oP their characteristic wpich were assigned the 6 and c conpiguration Hnmr spectra. of these epoxides yielded the stereoisomeric U-ketones 19 and 20.

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