Abstract
Synthesis of 4′-branched BCA analogues (5) was carried out. Stereospecific construction of the cis-disposed 4′-carbon-substituents and 5′-hydroxymethyl group was secured by employing the bicyclo[3.3.0]lactone 16 as a key intermediate, which was prepared by radical-mediated intramolecular SH2′ cyclization of the phenylselenomethyl ester 15. After manipulation of the double bond of 16, bis(Boc)adenine was introduced based on the Mitsunobu reaction of the allyl alcohol 24. Transformation of the lactone function of 27 allowed preparation of the 4′-hydroxymethyl (31), the 4′-vinyl (32), the 4′-cyano (34), and the 4′-ethynyl (35) derivatives. Anti-HIV and anti-HCV activities of the free nucleosides 36-38 were also examined.
| Original language | English |
|---|---|
| Pages (from-to) | 1494-1505 |
| Number of pages | 12 |
| Journal | Tetrahedron |
| Volume | 64 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - Feb 11 2008 |
Fingerprint
Keywords
- Carbocyclic nucleoside
- Mitsunobu reaction
- Radical cyclization
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Synthesis of (±)-9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (BCA) derivatives branched at the 4′-position based on intramolecular SH2′ cyclization. / Kumamoto, Hiroki; Takahashi, Nonoko; Shimamura, Tomomi; Tanaka, Hiromichi; Nakamura, Kazuo T.; Hamasaki, Takayuki; Baba, Masanori; Abe, Hiroshi; Yano, Masahiko; Kato, Nobuyuki.
In: Tetrahedron, Vol. 64, No. 7, 11.02.2008, p. 1494-1505.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis of (±)-9-[c-4, t-5-bis(hydroxymethyl)cyclopent-2-en-r-1-yl]-9H-adenine (BCA) derivatives branched at the 4′-position based on intramolecular SH2′ cyclization
AU - Kumamoto, Hiroki
AU - Takahashi, Nonoko
AU - Shimamura, Tomomi
AU - Tanaka, Hiromichi
AU - Nakamura, Kazuo T.
AU - Hamasaki, Takayuki
AU - Baba, Masanori
AU - Abe, Hiroshi
AU - Yano, Masahiko
AU - Kato, Nobuyuki
PY - 2008/2/11
Y1 - 2008/2/11
N2 - Synthesis of 4′-branched BCA analogues (5) was carried out. Stereospecific construction of the cis-disposed 4′-carbon-substituents and 5′-hydroxymethyl group was secured by employing the bicyclo[3.3.0]lactone 16 as a key intermediate, which was prepared by radical-mediated intramolecular SH2′ cyclization of the phenylselenomethyl ester 15. After manipulation of the double bond of 16, bis(Boc)adenine was introduced based on the Mitsunobu reaction of the allyl alcohol 24. Transformation of the lactone function of 27 allowed preparation of the 4′-hydroxymethyl (31), the 4′-vinyl (32), the 4′-cyano (34), and the 4′-ethynyl (35) derivatives. Anti-HIV and anti-HCV activities of the free nucleosides 36-38 were also examined.
AB - Synthesis of 4′-branched BCA analogues (5) was carried out. Stereospecific construction of the cis-disposed 4′-carbon-substituents and 5′-hydroxymethyl group was secured by employing the bicyclo[3.3.0]lactone 16 as a key intermediate, which was prepared by radical-mediated intramolecular SH2′ cyclization of the phenylselenomethyl ester 15. After manipulation of the double bond of 16, bis(Boc)adenine was introduced based on the Mitsunobu reaction of the allyl alcohol 24. Transformation of the lactone function of 27 allowed preparation of the 4′-hydroxymethyl (31), the 4′-vinyl (32), the 4′-cyano (34), and the 4′-ethynyl (35) derivatives. Anti-HIV and anti-HCV activities of the free nucleosides 36-38 were also examined.
KW - Carbocyclic nucleoside
KW - Mitsunobu reaction
KW - Radical cyclization
UR - http://www.scopus.com/inward/record.url?scp=37649007280&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=37649007280&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2007.11.038
DO - 10.1016/j.tet.2007.11.038
M3 - Article
AN - SCOPUS:37649007280
VL - 64
SP - 1494
EP - 1505
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 7
ER -