TY - JOUR
T1 - Unusual dimerization of 3-methylphenalen-1-one, leading to a chiral heptacyclic oxocin
AU - Pogodin, S.
AU - Thirumalaikumar, M.
AU - Cohen, S.
AU - Agranat, Isria
PY - 2005/11
Y1 - 2005/11
N2 - A diastereoselective reaction of 3-methyl-1H-phenalen-1-one (6) with Lawesson's reagent afforded 8a, 15a-dihydro-7,8a,16-trimethyl-7,16-epoxy-7H,15H,16H-naphtho[1,8-ef] phenaleno[1,2-b]oxocin-15-one (10), in 82% yield. The formation mechanism of 10 involves a Michael addition of a naphthopyrane intermediate to 6, followed by an intramolecular aldol condensation. The structure of a single enantiomer of 10 (7R, 8aR, 15aR, 16S or 7S, 8aS, 15aS, 16R) was elucidated by X-ray crystallography.
AB - A diastereoselective reaction of 3-methyl-1H-phenalen-1-one (6) with Lawesson's reagent afforded 8a, 15a-dihydro-7,8a,16-trimethyl-7,16-epoxy-7H,15H,16H-naphtho[1,8-ef] phenaleno[1,2-b]oxocin-15-one (10), in 82% yield. The formation mechanism of 10 involves a Michael addition of a naphthopyrane intermediate to 6, followed by an intramolecular aldol condensation. The structure of a single enantiomer of 10 (7R, 8aR, 15aR, 16S or 7S, 8aS, 15aS, 16R) was elucidated by X-ray crystallography.
KW - Chirality
KW - Diastereoselective reaction
KW - Lawesson's reagent
KW - Novel aromatic chemistry
KW - Phenalenes
KW - X-ray crystallography
UR - http://www.scopus.com/inward/record.url?scp=46149125749&partnerID=8YFLogxK
U2 - 10.2174/157017805774296867
DO - 10.2174/157017805774296867
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AN - SCOPUS:46149125749
SN - 1570-1786
VL - 2
SP - 640
EP - 643
JO - Letters in Organic Chemistry
JF - Letters in Organic Chemistry
IS - 7
ER -