TY - JOUR
T1 - Collective total synthesis of PPAPs
T2 - Total synthesis of clusianone via intramolecular cyclopropanation
AU - Uwamori, Masahiro
AU - Nakada, Masahisa
PY - 2013/7
Y1 - 2013/7
N2 - The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- And stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis of clusianone.
AB - The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence, which has been utilized for the total syntheses of nemorosone, garsubellin A, and hyperforin: intramolecular cyclopropanation, formation of a geminal dimethyl group, and regioselective ring opening of cyclopropane. Further elaboration, including chemo- And stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains, was employed to complete the total synthesis of clusianone.
KW - Clusianone
KW - Cyclopropanation
KW - Natural product
KW - Stereoselectivity
KW - Total synthesis
UR - http://www.scopus.com/inward/record.url?scp=84880843664&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84880843664&partnerID=8YFLogxK
U2 - 10.1177/1934578x1300800721
DO - 10.1177/1934578x1300800721
M3 - Review article
C2 - 23980429
AN - SCOPUS:84880843664
SN - 1934-578X
VL - 8
SP - 955
EP - 959
JO - Natural Product Communications
JF - Natural Product Communications
IS - 7
ER -