Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides
DOI: 10.14469/hpc/6103 Metadata
Created: 2019-09-16 13:42
Last modified: 2020-03-31 16:56
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Co-author: D. Christopher Braddock
Description
We report a relay cross metathesis (ReXM) reaction for the ascent of the terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated Δ6,7-functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene. Subsequent functional group manipulation allows for the method to be repeated in an iterative fashion. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products.
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/5771 | (S,E)-3-(5-(Allyloxy)-3-methylpent-3-en-1-yl)-2,2-dimethyloxirane (2) |
| 10.14469/hpc/5772 | (S)-9-(3,3-Dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienal (4) |
| 10.14469/hpc/5774 | (S)-9-(3,3-Dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dien-1-ol (7) |
| 10.14469/hpc/5779 | (S)-3-(9-(Allyloxy)-3,7-dimethylnona-3,7-dien-1-yl)-2,2-dimethyloxirane (8) |
| 10.14469/hpc/5780 | (S)-13-(3,3-Dimethyloxiran-2-yl)-3,7,11-trimethyltrideca-2,6,10-trienal (9) |
| 10.14469/hpc/5781 | (S)-13-(3,3-Dimethyloxiran-2-yl)-3,7,11-trimethyltrideca-2,6,10-trien-1-ol (10) |
| 10.14469/hpc/5784 | Ethyl 4-hydroxy-3-iodobenzoate (12) |
| 10.14469/hpc/5785 | Ethyl 4-ethoxy-3-iodobenzoate (13) |
| 10.14469/hpc/5786 | Ethyl (E)-3-(3,7-dimethylocta-2,6-dien-1-yl)-4-ethoxybenzoate (14) |
| 10.14469/hpc/5783 | (S)-3-(13-Bromo-3,7,11-trimethyltrideca-3,7,11-trien-1-yl)-2,2-dimethyloxirane (15) |
| 10.14469/hpc/5792 | Ethyl (S)-3-(13-(3,3-dimethyloxiran-2-yl)-3,7,11-trimethyltrideca-2,6,10-trien-1-yl)-4-ethoxybenzoate (16) |
| 10.14469/hpc/5788 | (S)-3-(13-(3,3-Dimethyloxiran-2-yl)-3,7,11-trimethyltrideca-2,6,10-trien-1-yl)-4-ethoxybenzoic acid (17) |
| 10.14469/hpc/5789 | (S)-3-(15-Bromo-14-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10-trien-1-yl)-4-ethoxybenzoic acid (18) |
| 10.14469/hpc/5790 | (R)-3-(14-Bromo-15-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10-trien-1-yl)-4-ethoxybenzoic acid (18a) |
| 10.14469/hpc/5791 | (S,7E,11E,15E)-4-(2-Bromopropan-2-yl)-1^4-ethoxy-7,11,15-trimethyl-3-oxa-1(1,3)-benzenacycloheptadecaphane-7,11,15-trien-2-one (19) |