Synthetic Anthracyclinones, XXXI. Total Synthesis of Racemic ϵe‐Rhodomycinones via Keto‐Ester Cyclization

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The keto esters 15 – 17b were prepared by regioselective alkylation of the anthraquinone acetals 12 – 14 followed by cleavage of the acetals and methyl ethers and esterification. The tetracyclic trans‐β‐hydroxy esters 25 – 27b were formed predominantly upon treatment of 15 – 17b with Triton B in pyridine, whereas lithium amides in THF gave only the cis‐hydroxy esters 28 and 29a. Stereoselective hydroxylation of 25 – 27b afforded the rhodomycinones 38 – 40a and 6 of natural configuration (cis‐2,4‐diols), while that of 28 – 30b gave the not naturally occurring trans‐2,4‐diols 41 – 43b.

Original languageEnglish
Pages (from-to)1506-1527
Number of pages22
JournalLiebigs Annalen der Chemie
Volume1986
Issue number9
DOIs
Publication statusPublished - 1 Jan 1986

Fingerprint Dive into the research topics of 'Synthetic Anthracyclinones, XXXI. Total Synthesis of Racemic ϵe‐Rhodomycinones via Keto‐Ester Cyclization'. Together they form a unique fingerprint.

Cite this