TY - JOUR
T1 - Silver-catalyzed benzannulation, part 2
T2 - Total synthesis of (1R,4S,11S)-8,19-dihydroxyserrulat-14-ene and (1R,4S,11S)-8-hydroxyserrulat-14-en-19-oic acid
AU - March, Taryn Lee
AU - Rudgley, Nicholas
AU - Perkins, Michael Victor
PY - 2022/11/9
Y1 - 2022/11/9
N2 - This paper reports the total synthesis of the serrulatane natural products (1R,4S,11S)-8,19-dihydroxyserrulat-14-ene (5.0% yield) and (1R,4S,11S)-8-hydroxyserrulat-14-en-19-oic acid (3.8% yield) via a silver-catalyzed 6-endo-dig benzannulation of an (−)-isopulegol derived ene-yne-ol in 17 steps. Analysis of the spectroscopic data as well as the specific rotations allowed for the confirmation of the stereochemistry at C1, C4 and C11 as (1R,4S,11S) for both natural products 8,19-dihydroxyserrulat-14-ene and 8-hydroxyserrulat-14-en-19-oic acid that were reported from the Australian desert plant, Eremophila neglecta.
AB - This paper reports the total synthesis of the serrulatane natural products (1R,4S,11S)-8,19-dihydroxyserrulat-14-ene (5.0% yield) and (1R,4S,11S)-8-hydroxyserrulat-14-en-19-oic acid (3.8% yield) via a silver-catalyzed 6-endo-dig benzannulation of an (−)-isopulegol derived ene-yne-ol in 17 steps. Analysis of the spectroscopic data as well as the specific rotations allowed for the confirmation of the stereochemistry at C1, C4 and C11 as (1R,4S,11S) for both natural products 8,19-dihydroxyserrulat-14-ene and 8-hydroxyserrulat-14-en-19-oic acid that were reported from the Australian desert plant, Eremophila neglecta.
KW - 5-alkoxy-1,5-enynes
KW - 6-endo-dig cyclisation
KW - Benzannulation
KW - serrulatane
KW - tetrahydronaphthalene
UR - http://www.scopus.com/inward/record.url?scp=85147870838&partnerID=8YFLogxK
U2 - 10.24820/ark.5550190.p011.815
DO - 10.24820/ark.5550190.p011.815
M3 - Article
AN - SCOPUS:85147870838
SN - 1551-7004
VL - 2022
SP - 188
EP - 204
JO - Arkivoc
JF - Arkivoc
IS - Part 4
ER -