Enantioselective synthesis of pyranonaphthoquinone antibiotics using a CBS reduction/cross-metathesis/oxa-Michael strategy
- 12 May 2011
- journal article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 9 (15), 5423-5430
- https://doi.org/10.1039/c1ob05595j
Abstract
The enantioselective syntheses of deoxydihydrokalafungin (5), cis-deoxydihydrokalafungin (6) and deoxykalafungin (7) are reported. The strategy was based on 4 key reactions: (1) CBS reduction of prochiral ketone 10 to introduce chirality at C-1, (2) radical allylation of quinone 9a, (3) cross-metathesis of dimethoxynaphthalene 13 with methyl acrylate, and (4) intramolecular oxa-Michael addition of alcohol 8 to form the core naphthopyran ring system. This novel approach delivers naphthopyrans possessing the natural trans-stereochemistry observed in the pyranonaphthoquinone family of antibiotics.This publication has 43 references indexed in Scilit:
- Intra‐ and Intermolecular Oxa‐Pictet–Spengler Cyclization Strategy for the Enantioselective Synthesis of Deoxy Analogues of (+)‐Nanomycin A Methyl Ester, (+)‐Eleutherin, (+)‐Allo‐Eleutherin, and (+)‐ThysanoneEuropean Journal of Organic Chemistry, 2010
- Synthesis of a C8 oxygenated pyranonaphthoquinone: a useful precursor to dimeric pyranonaphthoquinonesTetrahedron, 2008
- Total synthesis of (+)-kalafungin using a tandem Michael–Dieckmann approachTetrahedron Letters, 2007
- Bi(OTf)3-catalyzed allylation of quinones with allyltrimethylsilaneTetrahedron Letters, 2003
- Synthesis of 1,3-disubstituted naphtho[2,3-c]pyran-5,10-dionesTetrahedron, 2001
- Synthetic Strategies Towards Pyranonaphthoquinone AntibioticsTetrahedron, 2000
- A Series of Well‐Defined Metathesis Catalysts–Synthesis of [RuCl2(CHR′)(PR3)2] and Its ReactionsAngewandte Chemie, 1995
- A biomimetic synthesis of (±)-nanaomycin ATetrahedron Letters, 1990
- Synthesis of 4‐Methoxypropranolol, a Suitable Internal Standard for the Determination of Propranolol and 4‐Hydroxypropranolol by HPLCArchiv der Pharmazie, 1981
- Kalafungin, a New Antibiotic Produced by Streptomyces tanashiensis Strain KalaApplied and Environmental Microbiology, 1968