Novel Synthesis of Highly Functionalized 14-β-Hydroxysteroids Related to Batrachotoxin and Ouabain
- 10 January 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (3) , 832-838
- https://doi.org/10.1021/jo0355606
Abstract
The use of anionic polycyclization was investigated in an effort to develop a versatile and convergent synthesis of advanced tetracyclic intermediates of batrachotoxin and ouabain analogues. Two new 5-(trialkylsilyl)-2-cyclohexenones as A ring precursors and a new Nazarov intermediate (D ring precursor) were prepared for this purpose. The reaction of the unsaturated β-keto aldehyde A ring precursor with the enolate of the Nazarov intermediate afforded, after subsequent transformations, a 14-β-hydroxysteroid with complete control of stereochemistry.Keywords
This publication has 17 references indexed in Scilit:
- Cascade Polycyclization: Exploration of a Convergent Route to Access Various Tricyclic and Tetracyclic Products Related to SterolsThe Journal of Organic Chemistry, 2003
- A Convergent Synthesis of the Cardenolide Skeleton: Intramolecular Aldol Condensation via Reduction of α-BromoketonesThe Journal of Organic Chemistry, 2002
- Total Synthesis of ent-Cholesterol via a Steroid C,D-Ring Side-Chain SynthonThe Journal of Organic Chemistry, 2002
- Total Synthesis of (±)-Batrachotoxinin AJournal of the American Chemical Society, 1998
- Carbenoid Reactions in Rhodium(II)‐Catalyzed Decomposition of Iodonium YlidesHelvetica Chimica Acta, 1995
- A novel intramolecular cyclopropanation using iodonium ylidesJournal of the American Chemical Society, 1989
- Enantioselective ring construction with control of side-chain stereochemistry. Synthesis of (+)-isoneonepetalactoneThe Journal of Organic Chemistry, 1988
- Bis(trimethylsilyl) Sulfate Catalysis in γ-Lactonization of Cyclopropanecarboxylates Activated by Carbonyl Substituents on α-CarbonBulletin of the Chemical Society of Japan, 1984
- Batrachotoxin: Chemistry and PharmacologyScience, 1971
- A Superior Method for the Preparation of Alkyl 5-Oxo-5,6,7,8-tetrahydroindane-8-carboxylatesSynthesis, 1970