Total Synthesis of a Cytotoxic Acetogenin, Pyranicin
- 27 March 2003
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 5 (8) , 1353-1356
- https://doi.org/10.1021/ol034323m
Abstract
[structure: see text] The first total synthesis of a new cytotoxic acetogenin, pyranicin (1), is described. SmI(2)-induced reductive cyclization of beta-alkoxy acrylate 4 proceeded stereoselectively to give 16,20-syn-19,20-trans-THP derivative 14, which was efficiently transformed into the 19,20-cis-THP derivative 18 through Mitsunobu lactonization. Wittig reaction of the phosphonium salt 2 obtained therefrom with butenolide 3 at -78 degrees C followed by reduction and deprotection afforded 1 in good overall yield.Keywords
This publication has 11 references indexed in Scilit:
- Stereoselective total synthesis of muconinTetrahedron, 2003
- Stereoselective Total Synthesis of Mucocin, an Antitumor AgentAngewandte Chemie International Edition in English, 2002
- Total Synthesis of an Antitumor Agent, Mucocin, Based on the “Chiron Approach”The Journal of Organic Chemistry, 2002
- Efficient strategy for the iterative synthesis of trans-fused polycyclic ether via SmI2-induced reductive intramolecular cyclizationTetrahedron, 2002
- Mechanism of the double bond isomerization from Δ24(28) to Δ24(25) in sitosterol biosynthesis in higher plantsTetrahedron Letters, 1999
- Efficient Synthesis of trans-Fused Polycyclic Ethers Including Tetrahydropyrans and Oxepanes Based on SmI2-Induced Reductive CyclizationOrganic Letters, 1999
- Unusual bioactive annonaceous acetogenins from Goniothalamus giganteusTetrahedron, 1998
- Tandem Oxidative Cyclization with Rhenium Oxide. Total Synthesis of 17,18-bisepi-GoniocinJournal of the American Chemical Society, 1997
- 4-deoxyannomontacin and (2,4-cis and trans)-annomontacinone, new bioactive mono-tetrahydrofuran annonaceous acetogenins from Goniothalamus giganteusBioorganic & Medicinal Chemistry, 1997
- Stereodivergent total synthesis of N-acetylacosamone and N-benzoylristosamineThe Journal of Organic Chemistry, 1987