Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide
This work aimed to demonstrate the feasibility of two environmental-friendly reactions that developed in Loh’s research group in the racemic synthesis of dactylolide (2), a marine natural product which is a potential candidate for anti-cancer treatment. Syntheses of two major components of dactyloli...
| Main Author: | |
|---|---|
| Other Authors: | |
| Format: | Thesis |
| Language: | English |
| Published: |
2017
|
| Subjects: | |
| Online Access: | http://hdl.handle.net/10356/70603 |
| _version_ | 1826115610401046528 |
|---|---|
| author | Wong, Zhen Zhou |
| author2 | Liu Chuan Fa |
| author_facet | Liu Chuan Fa Wong, Zhen Zhou |
| author_sort | Wong, Zhen Zhou |
| collection | NTU |
| description | This work aimed to demonstrate the feasibility of two environmental-friendly reactions that developed in Loh’s research group in the racemic synthesis of dactylolide (2), a marine natural product which is a potential candidate for anti-cancer treatment. Syntheses of two major components of dactylolide, namely C1-C8 fragment (C3-2) and C9-C19 fragment (AB-1b-I) were achieved in this study with two key strategies, which were In(OTf)3-catalyzed intramolecular 2,5-oxonium-ene cyclization and Pd-catalyzed direct cross-coupling reaction. Both strategies provided access to southern 2,6-syn-4-exomethylene tetrahydropyran motif and northern conjugated dienoate structure respectively. C9-C19 fragment (AB-1b-I) was convergently synthesized from two parallel syntheses, which provided conjugated aldehyde A2 and homoallylic alcohol B2-2 as precursor for tetrahydropyran synthesis. On the other hand, synthesis of C1-C8 fragment (C3-2) was achieved with a 5-step transformation from epichlorohydrin. This established route utilized convergent strategy, catalytic bond-forming reactions and employed less hazardous chemicals, which showed greener access to target fragments. |
| first_indexed | 2024-10-01T03:58:17Z |
| format | Thesis |
| id | ntu-10356/70603 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:58:17Z |
| publishDate | 2017 |
| record_format | dspace |
| spelling | ntu-10356/706032021-03-20T12:57:47Z Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide Wong, Zhen Zhou Liu Chuan Fa Loh Teck Peng Interdisciplinary Graduate School (IGS) Nanyang Environment and Water Research Institute DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis This work aimed to demonstrate the feasibility of two environmental-friendly reactions that developed in Loh’s research group in the racemic synthesis of dactylolide (2), a marine natural product which is a potential candidate for anti-cancer treatment. Syntheses of two major components of dactylolide, namely C1-C8 fragment (C3-2) and C9-C19 fragment (AB-1b-I) were achieved in this study with two key strategies, which were In(OTf)3-catalyzed intramolecular 2,5-oxonium-ene cyclization and Pd-catalyzed direct cross-coupling reaction. Both strategies provided access to southern 2,6-syn-4-exomethylene tetrahydropyran motif and northern conjugated dienoate structure respectively. C9-C19 fragment (AB-1b-I) was convergently synthesized from two parallel syntheses, which provided conjugated aldehyde A2 and homoallylic alcohol B2-2 as precursor for tetrahydropyran synthesis. On the other hand, synthesis of C1-C8 fragment (C3-2) was achieved with a 5-step transformation from epichlorohydrin. This established route utilized convergent strategy, catalytic bond-forming reactions and employed less hazardous chemicals, which showed greener access to target fragments. Doctor of Philosophy (IGS) 2017-05-05T02:22:54Z 2017-05-05T02:22:54Z 2017 Thesis Wong, Z. Z. (2017). Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide. Doctoral thesis, Nanyang Technological University, Singapore. http://hdl.handle.net/10356/70603 10.32657/10356/70603 en 239 p. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis Wong, Zhen Zhou Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide |
| title | Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide |
| title_full | Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide |
| title_fullStr | Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide |
| title_full_unstemmed | Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide |
| title_short | Application of environmental-friendly reactions in high-value compound synthesis : synthetic studies towards the total synthesis of dactylolide |
| title_sort | application of environmental friendly reactions in high value compound synthesis synthetic studies towards the total synthesis of dactylolide |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis |
| url | http://hdl.handle.net/10356/70603 |
| work_keys_str_mv | AT wongzhenzhou applicationofenvironmentalfriendlyreactionsinhighvaluecompoundsynthesissyntheticstudiestowardsthetotalsynthesisofdactylolide |