A Nozaki-Hiyama-Kishi Ni(II)/Cr(II) Coupling Approach to the Phomactins

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1491-1494

  Mi, Baoyu ^a   Maleczka Jr , Robert E ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITHROMBOCYTIC AGENT; CHROMIUM; EPOXIDE; FUSED HETEROCYCLIC RINGS; GUANIDINE DERIVATIVE; NICKEL; PALAU'AMINE; PHOMACTIN A; PHOMACTIN D; SPIRO COMPOUND; THROMBOCYTE ACTIVATING FACTOR;

ANIMAL; ARTICLE; BIOLOGY; CHEMISTRY; DRUG ANTAGONISM; FUNGUS; HUMAN; SYNTHESIS;

ANIMALS; CHROMIUM; EPOXY COMPOUNDS; FUNGI; GUANIDINES; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; MARINE BIOLOGY; NICKEL; PLATELET ACTIVATING FACTOR; PLATELET AGGREGATION INHIBITORS; SPIRO COMPOUNDS;

EID: 0035902267     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015807q     Document Type: Article

References (42)

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35. See Supporting Information for details.
36. THF aided the solubility of 9.
37. Complete consumption of 10 occurred after 45 h, but the combined yield of 11 and 12 was only 29%.
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39. The nature of the phomactin skeleton makes representation of the relative stereochemistry through the use of wedged and dashed lines difficult and at time confusing. For example, refs 1b and 8 use dashed bonds for both the trans oriented C(3)-H and C(4)-Me groups of phomactins C (2), D (3), and allied structures.
40. The results of biological testing will be reported elsewhere.
41. Prolonged reaction with excess oxidant affords the diketone in 72% overall yield.
42. AMI semiempirical calculations suggest 16 to be ∼10 kcal/mol lower in energy than its trans-fused isomer.