The first enantioselective total synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether
- 26 January 2005
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 36 (12) , 1560-1562
- https://doi.org/10.1039/b418106a
Abstract
The first enantioselective synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether has been carried out in a convergent fashion by heterocycle-activated Julia olefination of a spiroacetal-containing sulfone fragment with a phthalide-containing aldehyde fragment. The total synthesis of (+)-spirolaxine methyl ether establishes the absolute stereochemistry of the natural product to be (3R,2″R,5″R,7″R).Keywords
This publication has 11 references indexed in Scilit:
- The modified Julia olefination: alkene synthesis via the condensation of metallated heteroarylalkylsulfones with carbonyl compoundsJournal of the Chemical Society, Perkin Transactions 1, 2002
- Total Synthesis of Reveromycin AOrganic Letters, 2000
- Total synthesis of the protein phosphatase inhibitor okadaic acidJournal of the Chemical Society, Perkin Transactions 1, 1998
- Catalytic, Enantioselective Addition of Allylsilanes to Aldehydes: Generation of a Novel, Reactive TiIV Complex from TiF4Angewandte Chemie International Edition in English, 1996
- Synthesis of (+)-Zaragozic Acid CJournal of the American Chemical Society, 1994
- Pigments of fungi. Part 38. Synthesis of austrocorticinic acid and (S)-(–)-austrocorticin; absolute stereochemistry of natural austrocorticinJournal of the Chemical Society, Perkin Transactions 1, 1994
- Helicobacter pylori: Its Role in DiseaseClinical Infectious Diseases, 1992
- An Efficient Synthesis of Enantiomerically Pure (R)-(2-Benzyloxyethyl)oxirane from (S)-Aspartic AcidSynthesis, 1992
- Spirolaxine and sporotricale: Two long-chain phthalides produced by Sporotrichum laxumPhytochemistry, 1990
- A convergent general synthetic protocol for syn-1,3-polyolsTetrahedron Letters, 1988