Abstract
An efficient method for the synthesis of versatile intermediates for biologically interesting 13-deoxy- and 9,13-dideoxyphorbol ester analogs is described. First, more efficient synthetic routes to the bicyclic ketones 7 and 8, which are well-known intermediates for the synthesis of 13- deoxyphorbols, than the previous one were established. Second, 7 and 8 were successfully converted to the intermediates 19, 25 and 27 for the synthesis of 9,13-dideoxyphorbols using Peterson reaction, oxymercuration and nitrile oxide cycloaddition as key steps.
| Original language | English |
|---|---|
| Pages (from-to) | 509-513 |
| Number of pages | 5 |
| Journal | Tetrahedron Letters |
| Volume | 41 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - Jan 22 2000 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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An efficient method for the synthesis of versatile intermediates leading to 13-deoxy- and 9,13-dideoxyphorbols. / Sekine, Akihiro; Kumagai, Naoya; Uotsu, Koichiro; Ohshima, Takashi; Shibasaki, Masakatsu.
In: Tetrahedron Letters, Vol. 41, No. 4, 22.01.2000, p. 509-513.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An efficient method for the synthesis of versatile intermediates leading to 13-deoxy- and 9,13-dideoxyphorbols
AU - Sekine, Akihiro
AU - Kumagai, Naoya
AU - Uotsu, Koichiro
AU - Ohshima, Takashi
AU - Shibasaki, Masakatsu
PY - 2000/1/22
Y1 - 2000/1/22
N2 - An efficient method for the synthesis of versatile intermediates for biologically interesting 13-deoxy- and 9,13-dideoxyphorbol ester analogs is described. First, more efficient synthetic routes to the bicyclic ketones 7 and 8, which are well-known intermediates for the synthesis of 13- deoxyphorbols, than the previous one were established. Second, 7 and 8 were successfully converted to the intermediates 19, 25 and 27 for the synthesis of 9,13-dideoxyphorbols using Peterson reaction, oxymercuration and nitrile oxide cycloaddition as key steps.
AB - An efficient method for the synthesis of versatile intermediates for biologically interesting 13-deoxy- and 9,13-dideoxyphorbol ester analogs is described. First, more efficient synthetic routes to the bicyclic ketones 7 and 8, which are well-known intermediates for the synthesis of 13- deoxyphorbols, than the previous one were established. Second, 7 and 8 were successfully converted to the intermediates 19, 25 and 27 for the synthesis of 9,13-dideoxyphorbols using Peterson reaction, oxymercuration and nitrile oxide cycloaddition as key steps.
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UR - http://www.scopus.com/inward/citedby.url?scp=0034700883&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(99)02103-6
DO - 10.1016/S0040-4039(99)02103-6
M3 - Article
VL - 41
SP - 509
EP - 513
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 4
ER -