Neoisostegane, a new bisbenzocyclooctadienolactonic lignan fromSteganotaenia araliacea, hochst.Tetrahedron Lett., 24, 197, (1983).

Neoisostegane, a New Bisbenzocyclooctadiene Lignan Lactone from Steganotaenia araliacea

“…32.4 ppm). This implied that the environment of C-8 in neoisostegane (1) was significantly different from 2 and 3. This was explained by the presence of a methoxyl substituent at C-9 rather than at C-12.…”

“…In the course of separate investigations of two different collections of Steganotaenia araliacea Hochst. (Apiaceae), one from the Republic of Guinea and one from Ethiopia, a new bisbenzocyclooctadiene lignan lactone has been isolated (1,2). Unlike the lignans of this type previously isolated by Kupchan and co-workers (3) from S. araliacea, neoisostegane (1) bears no functionality at C-5.2 Extracts of the two collections of S. araliacea were prepared according to previously established protocols (3,4).…”

“…(Apiaceae), one from the Republic of Guinea and one from Ethiopia, a new bisbenzocyclooctadiene lignan lactone has been isolated (1,2). Unlike the lignans of this type previously isolated by Kupchan and co-workers (3) from S. araliacea, neoisostegane (1) bears no functionality at C-5.2 Extracts of the two collections of S. araliacea were prepared according to previously established protocols (3,4). Preparative tic of appropriate fractions derived as described in the Experimental section gave, in each case, pure neoisostegane (1) as a crystalline solid.…”

“…Unlike the lignans of this type previously isolated by Kupchan and co-workers (3) from S. araliacea, neoisostegane (1) bears no functionality at C-5.2 Extracts of the two collections of S. araliacea were prepared according to previously established protocols (3,4). Preparative tic of appropriate fractions derived as described in the Experimental section gave, in each case, pure neoisostegane (1) as a crystalline solid. 3 High resolution ms established the molecular formula of 1 as C23H2607 (mlz 414.1671 [LSO], 414.1702 [VCU]; caled 414.1679).…”

Asymmetric synthesis of lignans of the dibenzylbutanediol and tetrahydrodibenzocyclooctene series

“…[a]h8 -32.2 (c 2.350, CHCl,) (Found: C, 67.55; H, 7.7. C22H3006 requires C, 67.79; H, 7.69%); v,,,(neat)/cm-' 3400 (OH); A,,,(MeOH)/nm 316.9 (E 6468); see Tables 3 and 4 for 'H and I3C NMR data; m/z 390 (M", 5%), 373 (32), 355 (17) and 151 (ArCH,', 100%) (Found: M+, 390.2040. C2,H3,06 requires M + , 390.2042).…”