01085nas a2200169 4500008004100000022001400041245003600055210003600091260000900127300001400136490000700150520062200157100002000779700002400799700002400823856006800847 2026 eng d a0022-326300aTotal synthesis of triplinone F0 aTotal synthesis of triplinone F cAPR  a5694-56980 v913 a

The first total synthesis of triplinone F, along with its C11 epimer, has been executed to establish, inter alia, the stereochemistry of C11 and its complete absolute configuration. The terminal styrene unit was added by cross-metathesis, whereby 1,3-diol units on either side of the central olefin were taken from malic acid enantiomers and coupled by a Yamaguchi alkyne-epoxide opening protocol. The C11 stereochemistry was manipulated by Noyori asymmetric ynone reduction. The Z-selective reduction of alkynoate and acid-catalyzed lactonization forged the right-hand-side 5,6-dihydro-delta-pyrone unit.

1 aShet, Manoj, N.1 aWabale, Krishna, R.1 aRamana, Chepuri, V. uhttps://library.ncl.res.in/content/total-synthesis-triplinone-f