Asymmetric Synthesis of Calyculin C. 2. Synthesis of the C26−C37 Fragment and Model Wittig Couplings
- 1 January 1996
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (18) , 6153-6161
- https://doi.org/10.1021/jo960315q
Abstract
We report our synthesis of the C26−C37 fragment of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C (1). Outlined in this paper are synthetic approaches to the two components based on disconnection at the C33−N3 amide bond. We report the successful synthesis of the C33−C37 aza-sugar derived from d-lyxose which was coupled onto a C26−C32 aminooxazole originating from l-pyroglutamic acid. Elaboration of the resulting amide to a fully deprotected C26−C37 fragment of calyculin C completed our synthesis. This provided an appropriate phosphonium salt for use in a Wittig olefination for joining both halves of the natural product.Keywords
This publication has 20 references indexed in Scilit:
- Total synthesis of (+)-calyculin AJournal of the American Chemical Society, 1992
- Synthesis of trans-4-alkenyl oxazolesTetrahedron Letters, 1991
- Reversal of aldehyde diastereofacial selectivity in a methyl ketone aldol reaction. Application to the synthesis of the calyculin spiroketalTetrahedron Letters, 1990
- Synthesis of fragments of a streptococcus pneumoniae type-specific capsular polysaccharideTetrahedron, 1989
- Bioactive marine metabolites. 24. Isolation and structure elucidation of calyculins B, C, and D, novel antitumor metabolites, from the marine sponge Discodermia calyxThe Journal of Organic Chemistry, 1988
- Bioactive marine metabolites. Part 16. Calyculin A. A novel antitumor metabolite from the marine sponge Discodermia calyxJournal of the American Chemical Society, 1986
- Asymmetric synthesis of quaternary carbon centersJournal of the American Chemical Society, 1984
- 520. The chemistry of the triterpenes and related compounds. Part XVIII. Elucidation of the structure of polyporenic acid CJournal of the Chemical Society, 1953
- 13. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycolsJournal of the Chemical Society, 1946
- Zur Kenntnis des Normal‐ und IsopropylaminsEuropean Journal of Inorganic Chemistry, 1917