Total synthesis of (+)-grandiamide D, dasyclamide and gigantamide A from a Baylis–Hillman adduct: A unified biomimetic approach

• Andivelu Ilangovan and
• Shanmugasundar Saravanakumar

Beilstein J. Org. Chem. 2014, 10, 127–133, doi:10.3762/bjoc.10.9

• , (+)-grandiamide D, dasyclamide and gigantamide A, isolated from leaves of Aglaia gigantea, by making use of a common synthetic intermediate prepared by the Baylis–Hillman reaction. Asymmetric synthesis of the natural (+)-grandiamide D was accomplished from camphor sultam. Keywords: Baylis–Hillman reaction

• ; dasyclamide; gigantamide A; (+)-grandiamide D; natural products; putrescine bisamides; Introduction Putrescine bisamides are one of the important naturally occurring polyamine alkaloids found in open chain and cyclic forms. The genera Aglaia are the richest source of putrescine bisamides. The cyclic 2

• compound, no other literature precedence is available till now. Duong et al. have isolated three cinnamoyl bisamide derivatives, two new compounds grandiamide D, gigantamide A and the known compound dasyclamide (Figure 2) from the leaves of Aglaia gigantea [7]. Even though the structures were determined by