Synthesis of the ring system of phomactin D using a Suzuki macrocyclization

Organic Letters

Volumn 2, Issue 17, 2000, Pages 2687-2690

  Kallan, Nicholas C ^a   Halcomb, Randall L ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; EPOXIDE; PHOMACTIN D; THROMBOCYTE ACTIVATING FACTOR;

ARTICLE; CYCLIZATION; DRUG ANTAGONISM; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; EPOXY COMPOUNDS; INDICATORS AND REAGENTS; PLATELET ACTIVATING FACTOR; STEREOISOMERISM;

EID: 0034710507     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0062345     Document Type: Article

References (33)

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21. The relative configuration of the stereocenters of 18 was determined using NOE difference NMR experiments. An NOE was observed between the protons of the methyls C-19 and C-20 and between the C-19 methyl and H-15, indicating that both methyls and H-15 must be on the same face of the cyclohexane. Also, H-15 had only small coupling constants and H-1 had one large coupling constant (to H-14ax) and two small ones, indicating that H-1 must be axial and H-15 must be equatorial. See Supporting Information for complete data.
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23. Prepared in a manner analogous to that of 1-iodo-2-methyl-(1Z.3)-butadiene: Ma, S.; Negishi, E. J. Org. Chem. 1997, 62, 784-785.
24. The relative configuration of the carbon bearing the TBS ether in the major diastereomer 21 was assigned on the basis of analogy to a derivative with slightly different side chains on the cyclohexane ring whose structure was unambiguously proven by X-ray crystallography. Also, the NMR spectral characteristics (chemical shifts, splitting patterns, and coupling constants) of the protons on the cyclohexane ring for each of the two compounds were virtually identical.
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33. A simultaneous publication describing this transformation has come to our attention: Chemler, S. R.; Danishefsky, S. J. Org. Lett. 2000, 2, 2695.