Total synthesis of natural and unnatural lamellarins with saturated and unsaturated D-rings

Journal of Organic Chemistry

Volumn 71, Issue 25, 2006, Pages 9440-9448

  Ploypradith, Poonsakdi ^a   Petchmanee, Thaninee ^a   Sahakitpichan, Poolsak ^a   Litvinas, Nichole D ^c   Ruchirawat, Somsak ^a,b  

^a Toxicology and Management of Chemicals   (Thailand)

^b MAHIDOL UNIVERSITY   (Thailand)

^c STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; COLUMN CHROMATOGRAPHY; OXIDATION;

HYDROGENOLYSIS; LACTONIZATION; LAMELLARINS; SATURATED LAMELLARIN ACETATES;

SYNTHESIS (CHEMICAL);

ACETIC ACID DERIVATIVE; CINNAMIC ACID DERIVATIVE; ISOQUINOLINE DERIVATIVE; LAMELLARIN DERIVATIVE; NATURAL PRODUCT; NITRO DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; COLUMN CHROMATOGRAPHY; HYDROGENOLYSIS; LACTONIZATION; MICHAEL ADDITION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

COUMARINS; CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; ISOQUINOLINES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY;

EID: 33845530699     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061810h     Document Type: Article

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42. Exceptions to this analysis are lamellarins H, S, Z, β, γ, and φ, which contain at least one catechol moiety as a peripheral aromatic group, and lamellarins O, P, Q, and R, which contain the "open structure".
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47. 4NBr was not effective.
48. Longer reaction times resulted in much lower yields presumably from base-mediated opening of the lactone and possibly subsequent decarboxylation of the pyrrole-2-carboxylate (Scheme 5) upon acidification of the crude mixture.