Abstract
From 3β,14-dihydroxy-5β,14β-card-20(22)-enolide (digitoxigenin) (III), new formal total syntheses of canarigenin [3β,14-dihydroxy-14β-carda-4,20(22)-dienolide] (IIa) and uzarigenin [3β,14-dihydroxy-5α,14β-card-20(22)-enolide] (Ic) have been completed. The route found most convenient involved direct oxidation of digitoxigenin (III) with t-butyl hypochlorite to yield the 4β-chloro-3-ketone (IVb). Dehydrohalogenation to the 4-en-3-one (canarigenone) (V) was followed by selective reduction with lithium hydrido-tri-t-butoxyaluminate to afford canarigenin (IIa) and with lithium borohydride to yield uzarigenin (Ic).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 1972-1976 |
| Number of pages | 5 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| Issue number | 19 |
| State | Published - 1975 |
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ASJC Scopus subject areas
- Chemistry(all)
- Medicine(all)
Cite this
Steroids and related natural products. Part XCI. Synthesis of the cardenolides canarigenin and uzarigenin. / Kamano, Yoshiaki; Pettit, George; Tozawa, Machiko.
In: Journal of the Chemical Society, Perkin Transactions 1, No. 19, 1975, p. 1972-1976.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Steroids and related natural products. Part XCI. Synthesis of the cardenolides canarigenin and uzarigenin
AU - Kamano, Yoshiaki
AU - Pettit, George
AU - Tozawa, Machiko
PY - 1975
Y1 - 1975
N2 - From 3β,14-dihydroxy-5β,14β-card-20(22)-enolide (digitoxigenin) (III), new formal total syntheses of canarigenin [3β,14-dihydroxy-14β-carda-4,20(22)-dienolide] (IIa) and uzarigenin [3β,14-dihydroxy-5α,14β-card-20(22)-enolide] (Ic) have been completed. The route found most convenient involved direct oxidation of digitoxigenin (III) with t-butyl hypochlorite to yield the 4β-chloro-3-ketone (IVb). Dehydrohalogenation to the 4-en-3-one (canarigenone) (V) was followed by selective reduction with lithium hydrido-tri-t-butoxyaluminate to afford canarigenin (IIa) and with lithium borohydride to yield uzarigenin (Ic).
AB - From 3β,14-dihydroxy-5β,14β-card-20(22)-enolide (digitoxigenin) (III), new formal total syntheses of canarigenin [3β,14-dihydroxy-14β-carda-4,20(22)-dienolide] (IIa) and uzarigenin [3β,14-dihydroxy-5α,14β-card-20(22)-enolide] (Ic) have been completed. The route found most convenient involved direct oxidation of digitoxigenin (III) with t-butyl hypochlorite to yield the 4β-chloro-3-ketone (IVb). Dehydrohalogenation to the 4-en-3-one (canarigenone) (V) was followed by selective reduction with lithium hydrido-tri-t-butoxyaluminate to afford canarigenin (IIa) and with lithium borohydride to yield uzarigenin (Ic).
UR - http://www.scopus.com/inward/record.url?scp=0016647353&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0016647353&partnerID=8YFLogxK
M3 - Article
C2 - 1238419
AN - SCOPUS:0016647353
SP - 1972
EP - 1976
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1470-4358
IS - 19
ER -