Divergent Synthesis of 17-nor-Cephalotane Diterpenoids through Developed Ynol-diene Cyclization
The diversity of complex molecular structures of Cephalotaxus diterpenoids poses great challenges in uncovering the pharmaceutical potential of these natural products. As a subfamily of Cephalotaxus diterpenoids, 17-nor-cephalotane diterpenoids possess polycyclic frameworks with seven-membered A ring bearing different oxidation states. On the basis of a novel ynol-diene cyclization developed as a rapid access to tropone unit, a concise and divergent strategy to 17-nor-cephalotane diterpenoids has been successfully established. Combining with a bioinspired stereoselective dual hydrogenation, the enantioselective total synthesis of (+)-3-deoxyfortalpinoid F, (+)-harringtonolide, (−)-fortalpinoids M/N/P, and analog (−)-20-deoxycephinoid P have been achieved in 14-17 linear longest steps starting from commercially available materials..
| Medienart: |
|
|---|
Preprint| Erscheinungsjahr: |
2024 |
|---|---|
| Erschienen: |
2024 |
| Enthalten in: |
chemRxiv.org - (2024) vom: 12. Apr. Zur Gesamtaufnahme - year:2024 |
|---|
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
Sun, Zezhong [VerfasserIn] |
|---|
| Links: |
Volltext [kostenfrei] |
|---|
| Themen: |
|---|
| doi: |
10.26434/chemrxiv-2024-85cxs-v2 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
XCH043251757 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | XCH043251757 | ||
| 003 | DE-627 | ||
| 005 | 20240413103103.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 240413s2024 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.26434/chemrxiv-2024-85cxs-v2 |2 doi | |
| 035 | |a (DE-627)XCH043251757 | ||
| 035 | |a (chemrXiv)10.26434/chemrxiv-2024-85cxs-v2 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a Sun, Zezhong |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Divergent Synthesis of 17-nor-Cephalotane Diterpenoids through Developed Ynol-diene Cyclization |
| 264 | 1 | |c 2024 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a Computermedien |b c |2 rdamedia | ||
| 338 | |a Online-Ressource |b cr |2 rdacarrier | ||
| 520 | |a The diversity of complex molecular structures of Cephalotaxus diterpenoids poses great challenges in uncovering the pharmaceutical potential of these natural products. As a subfamily of Cephalotaxus diterpenoids, 17-nor-cephalotane diterpenoids possess polycyclic frameworks with seven-membered A ring bearing different oxidation states. On the basis of a novel ynol-diene cyclization developed as a rapid access to tropone unit, a concise and divergent strategy to 17-nor-cephalotane diterpenoids has been successfully established. Combining with a bioinspired stereoselective dual hydrogenation, the enantioselective total synthesis of (+)-3-deoxyfortalpinoid F, (+)-harringtonolide, (−)-fortalpinoids M/N/P, and analog (−)-20-deoxycephinoid P have been achieved in 14-17 linear longest steps starting from commercially available materials. | ||
| 650 | 4 | |a Chemistry |7 (dpeaa)DE-84 | |
| 650 | 4 | |a 540 |7 (dpeaa)DE-84 | |
| 700 | 1 | |a Shu, Xin |e verfasserin |4 aut | |
| 700 | 1 | |a Ma, Fuli |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Ao |e verfasserin |4 aut | |
| 700 | 1 | |a Li, Yali |e verfasserin |4 aut | |
| 700 | 1 | |a Jin, Shuang |e verfasserin |4 aut | |
| 700 | 1 | |a Wang, Yunxia |e verfasserin |4 aut | |
| 700 | 1 | |a Hu, Xiangdong |e verfasserin |0 (orcid)0000-0002-8644-6454 |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t chemRxiv.org |g (2024) vom: 12. Apr. |
| 773 | 1 | 8 | |g year:2024 |g day:12 |g month:04 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.26434/chemrxiv-2024-85cxs-v2 |m X:VERLAG |x 0 |z kostenfrei |3 Volltext |
| 912 | |a GBV_XCH | ||
| 951 | |a AR | ||
| 952 | |j 2024 |b 12 |c 04 | ||