Total synthesis of the microtubule stabilizing antitumor agent laulimalide and some nonnatural analogues: The power of sharpless' asymmetric epoxidation

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3026-3042

  Ahmed, Anjum ^a   Hoegenauer, E Kate ^a   Enev, Valentin S ^a   Hanbauer, Martin ^a   Kaehlig, Hanspeter ^a   Ohler, Elisabeth ^a   Mulzer, Johann ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

SHARPLESS ASYMMETRIC EPOXIDATION (SAE);

BIOCHEMISTRY; DERIVATIVES; MOLECULAR STRUCTURE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TUMORS;

ORGANIC COMPOUNDS;

ALDEHYDE DERIVATIVE; ANTINEOPLASTIC AGENT; DEOXYLAULIMALIDE; EPOTHILONE B; LAULIMALIDE; PACLITAXEL; SILANE DERIVATIVE; TARTARIC ACID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION; DERIVATIZATION; DRUG SYNTHESIS; EPOXIDATION; MICROTUBULE; MOLECULAR STABILITY; SPONGE (PORIFERA); STEREOCHEMISTRY;

ANIMALS; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CHEMISTRY, ORGANIC; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; EPOTHILONES; FEMALE; HUMANS; INDICATORS AND REAGENTS; MITOTIC SPINDLE APPARATUS; MOLECULAR STRUCTURE; PACLITAXEL; PORIFERA; STEREOISOMERISM; TAXOIDS; TUMOR CELLS, CULTURED;

EID: 0037453610     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026743f     Document Type: Article

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146. Attempted desilylation of 63 with TBAF resulted in decomposition of the phosphonate moiety.
147. 19c
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155. 12b,c by lactonization of a hydroxy alkynoic acid.
156. 27 epoxyaldehyde fragments analogous to 69 but with (19R)-stereochemistry, as the coupling partners. To date, the critical allylation reaction was performed only by Crimmins and gave a rather low 3:1 stereoselectivity.
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