Bioinspired Asymmetric Synthesis of Hispidaninâ
A.
Angew Chem Int Ed Engl
; 56(21): 5844-5848, 2017 05 15.
Article
em En
| MEDLINE
| ID: mdl-28332749
ABSTRACT
The first enantiospecific synthesis of hispidaninâ
A (4), a dimeric diterpenoid from the rhizomes of Isodon hispida, was achieved with a longest linear sequence of 12â
steps in 6.5 % overall yield. A key component is the use of the abundant and naturally occurring diterpenoids (+)-sclareolide and (+)-sclareol as starting materials, which enables the gram-scale preparation of the key intermediates totarane (1) and s-trans-12E,14-labdadien-20,8ß-olide (2). Subsequently a thermal or an erbium-catalyzed intermolecular Diels-Alder reaction of totarane (1) with labdadienolide (2) provide convergent and rapid access to the natural product hispidaninâ
A (4). The synthetic studies have offered significant impetus for the efficient construction of these architecturally complex natural products.
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Base de dados:
MEDLINE
Assunto principal:
Diterpenos
Idioma:
En
Ano de publicação:
2017
Tipo de documento:
Article