Abstract
The nitrones derived from β-allyloxyaldehydes with a β-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a γ-allyloxyaldehyde with a γ-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose.
| Original language | English |
|---|---|
| Pages (from-to) | 1323-1340 |
| Number of pages | 18 |
| Journal | Tetrahedron Asymmetry |
| Volume | 7 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 1996 Jan 1 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry
Cite this
Synthetic studies on zoapatanol : Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy. / Shing, Tony Kung Ming; Wong, Ching Hung; Yip, Ting.
In: Tetrahedron Asymmetry, Vol. 7, No. 5, 01.01.1996, p. 1323-1340.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthetic studies on zoapatanol
T2 - Construction of oxepanes via an intramolecular 1,3-dipolar cycloaddition strategy
AU - Shing, Tony Kung Ming
AU - Wong, Ching Hung
AU - Yip, Ting
PY - 1996/1/1
Y1 - 1996/1/1
N2 - The nitrones derived from β-allyloxyaldehydes with a β-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a γ-allyloxyaldehyde with a γ-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose.
AB - The nitrones derived from β-allyloxyaldehydes with a β-quaternary centre cyclized to give six- instead of seven-membered O-heterocycles exclusively whereas a nitrile oxide derived from a γ-allyloxyaldehyde with a γ-quaternary centre cyclized to yield an oxepane ring as the sole product. Using the latter intramolecular nitrile oxide cycloaddition as the key step, optically active oxepane 5, which is a suitable intermediate for a synthesis of zoapatanol 1, has been constructed from D-glucose.
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UR - http://www.scopus.com/inward/citedby.url?scp=0029953154&partnerID=8YFLogxK
U2 - 10.1016/0957-4166(96)00149-8
DO - 10.1016/0957-4166(96)00149-8
M3 - Article
AN - SCOPUS:0029953154
VL - 7
SP - 1323
EP - 1340
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 5
ER -