Abstract
The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.
| Original language | English |
|---|---|
| Pages (from-to) | 2800-2803 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 59 |
| Issue number | 29 |
| DOIs | |
| Publication status | Published - Jul 18 2018 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
Cite this
Synthesis of anti-tubercular marine alkaloids denigrins A and B. / Karak, Milandip; Oishi, Tohru; Torikai, Kohei.
In: Tetrahedron Letters, Vol. 59, No. 29, 18.07.2018, p. 2800-2803.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of anti-tubercular marine alkaloids denigrins A and B
AU - Karak, Milandip
AU - Oishi, Tohru
AU - Torikai, Kohei
PY - 2018/7/18
Y1 - 2018/7/18
N2 - The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.
AB - The first synthesis of anti-tubercular marine alkaloids denigrins A and B were accomplished in three and five steps and 62% and 31% overall yields respectively, from maleic anhydride. The key features of the synthesis include efficient Mizoroki-Heck reaction, geometry-controlled vinylogous aldol condensation, and one-pot lactamization. The synthesis first demonstrates the serviceability of maleic anhydride in palladium-catalyzed cross-coupling reactions with diaryliodonium salt.
UR - http://www.scopus.com/inward/record.url?scp=85048326871&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85048326871&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2018.06.013
DO - 10.1016/j.tetlet.2018.06.013
M3 - Article
VL - 59
SP - 2800
EP - 2803
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 29
ER -