TY - JOUR
T1 - Total Synthesis of Gramistilbenoids A, B, and C
AU - Harmalkar, Dipesh S.
AU - Lu, Qili
AU - Lee, Kyeong
N1 - Publisher Copyright:
© 2018 American Chemical Society and American Society of Pharmacognosy.
PY - 2018/4/27
Y1 - 2018/4/27
N2 - Stilbenes are biologically active metabolites of plants that have the potential to attenuate a broad range of human diseases. Gramistilbenoids are a class of natural products with a stilbene skeleton, isolated from the bamboo orchid (Arundina graminifolia), and with significant cytotoxicity against cancer cell lines (NB4, A549, SHSY5Y, PC3, and MCF7). These are the first identified naturally occurring diphenylethylenes to possess a hydroxyethyl unit. However, some of these compounds are not abundant in nature, and thus, their synthesis is advantageous. This paper reports the first synthesis of gramistilbenoids A (1), B (2), and C (3), with overall yields of 10, 2, and 8% respectively. These natural products were synthesized using key reactions, such as Horner-Wadsworth-Emmons olefination, Stille coupling, and hydroboration-oxidation.
AB - Stilbenes are biologically active metabolites of plants that have the potential to attenuate a broad range of human diseases. Gramistilbenoids are a class of natural products with a stilbene skeleton, isolated from the bamboo orchid (Arundina graminifolia), and with significant cytotoxicity against cancer cell lines (NB4, A549, SHSY5Y, PC3, and MCF7). These are the first identified naturally occurring diphenylethylenes to possess a hydroxyethyl unit. However, some of these compounds are not abundant in nature, and thus, their synthesis is advantageous. This paper reports the first synthesis of gramistilbenoids A (1), B (2), and C (3), with overall yields of 10, 2, and 8% respectively. These natural products were synthesized using key reactions, such as Horner-Wadsworth-Emmons olefination, Stille coupling, and hydroboration-oxidation.
UR - http://www.scopus.com/inward/record.url?scp=85046292500&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.7b00865
DO - 10.1021/acs.jnatprod.7b00865
M3 - Article
C2 - 29613790
AN - SCOPUS:85046292500
SN - 0163-3864
VL - 81
SP - 798
EP - 805
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -