The Total Synthesis of (-)-Lemonomycin

Journal of the American Chemical Society

Volumn 125, Issue 49, 2003, Pages 15000-15001

  Ashley, Eric R ^a   Cruz, Ernest G ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; LEMONOMYCIN; QUINOCARCIN; SAFRAMYCIN; TRABECTEDIN; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CYCLIZATION; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; FERMENTATION; NONHUMAN; STAPHYLOCOCCUS AUREUS;

ANTIBIOTICS, ANTINEOPLASTIC; CYCLIZATION; STEREOISOMERISM; TETRAHYDROISOQUINOLINES;

EID: 0345098343     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039223q     Document Type: Article

References (19)

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10. To facilitate isolation of the desired isomer, we have adopted an in situ procedure that involves reduction of the aldehyde to a 1° alcohol and protection as a TIPS ether. The overall yield for this three-step transformation is 72% and has been carried out on a 10 g scale.
11. (a) Unless otherwise noted, all reactions were performed at ambient temperature (20 °C) for 1 h or less.
12. (b) See Supporting Information for full experimental details.
13. The relative configuration has been established by X-ray crystallographic analysis of a derivative; see the Supporting Information.
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19. Although we have not fully characterized any other products of this PS cyclization, purification by HPLC must remove any trace diastereomers (<3%) resulting from the initial cycloaddition (94% ee).