Synthesis of the C1C16 fragment of the marine toxin, laulimalide
✍ Scribed by Atsushi Shimizu; Shigeru Nishiyama
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 184 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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A synthesis of the C(1) C( 16) fragment 43 of the bryostatins is reported which features a stereoselective equivalent of an 'ene' reaction between the allylsilane 35 and the alkynone 33 and the stereoselective conjugate addition-cyclisation of the dienyl ketone 36 to give the acetal 39 after acetali
The C 15 -C 28 fragment of the paclitaxel-like antimicrotubule agent laulimalide has been synthesized in 12 linear steps from known epoxide 5, with an overall yield of 16%. The methyldihydropyran ring of the side chain was efficiently prepared using ring-closing olefin metathesis chemistry. The 19,2
A stereocontrolled synthesis of the C15±C27 fragment of laulimalide is described. Key features are a divergent±convergent synthesis from (R)-glycidol, an interesting formation of a trisubstituted double bond via ring closing metathesis with Grubbs' ruthenium catalyst and a site selective protection