Construction of the Tetracyclic Core of

Calyciphylline B-Type Daphniphyllum Alkaloids

Chenglong Du, Jing Fang, Jinyan Chen, Zaimin Liu,

Huilin Li, Xiaolei Wang, Xingang Xie, and Xuegong She

State Key Laboratory of Applied Organic Chemistry, College of

Chemistry and Chemical Engineering, Lanzhou University,
Lanzhou 730000, P.R. China

DOI: 10.1021/acs.orglett.9b03322
Org. Lett. 2019, 21, 8718–8721
Estructura de alcaloides del tipo Calyciphylline B

Plants of the Daphniphyllum genus are widely

distributed from tropical to subtropical Asia and
have long been used as Chinese traditional
herbal medicine to treat many common
diseases.
They exhibit broad important activities such as
vasorelaxant, anti-HIV, anticarcinogenic, and
cytotoxic activities.
Intensive phytochemical studies led to the
isolation of a large and growing number of
polycyclic alkaloids with overwhelming
structural complexity. Daphniphyllum alkaloids
are classified into more than 20 substructural
types according to their structure character

Angew. Chem., Int. Ed. 2016, 55, 2577– 2581, DOI: 10.1002/anie.201510861
Org. Lett. 2017, 19, 3739– 3742, DOI: 10.1021/acs.orglett.7b01566
J. Am. Chem. Soc. 2019, 141, 8431– 8435, DOI: 10.1021/jacs.9b03576
Análisis retrosintético de alcaloides del tipo
Calyciphylline B

A
E
B

C
Análisis retrosintético de 3
Análisis retrosintético de 4
 Síntesis del precursor 5 a partir de caprolactone

A,
Caprolactone B, 5
B
Síntesis del precursor 3 a partir de 5
 Síntesis del precursor 6 a partir del
ácido aspártico

L-aspartic acid

6´ (serie L)
Síntesis del precursor 4 a partir de 6
Construcción del “core” tetracíclico