Flexible and convergent total synthesis of cyclotheonamide B

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 3880-3889

  Bastiaans, Harold M M ^a,c   Van der Baan, Juul L ^a   Ottenheijm, Harry C J ^a,b  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b NV ORGANON   (Netherlands)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; CYCLOTHEONAMIDE B; PENTAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030852154     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961447m     Document Type: Article

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20. The route described in this paper was also used to prepare a series of analogues. Their synthesis and biological activity will be reported elsewhere.
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44. TMS-triflate and TBDMS-triflate are known to effect trans-esterification of Boc groups to give TMS- and TBDMS-earbamates. When only deprotection is required, the use of TMS-triflate is superior to TBDMS-triflate because TMS-carbamates are more readily cleaved than TBDMS-carbamates; however, TBDMS-triflate appears to be more selective; e.g.: (a) Borgulya, J.; Bernauer, K. Synlett 1980, 545. (b) Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543. (c) Sakaitani, M.; Ohfune, Y. J. Org. Chem. 1990, 55, 870.
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