Methods and compositions for terpenoid tricycloalkane synthesis

Patent metadata

Field	Value
Publication number	US-11008283-B2
Application number	US-202017013902-A
Country	US
Kind code	B2
Filing date	Sep 8, 2020
Priority date	May 16, 2018
Publication date	May 18, 2021
Grant date	May 18, 2021

Abstract

In one aspect, the disclosure relates to methods for preparation of intermediates useful for the preparation of terpenoid cores. In a further aspect, the disclosed methods pertain to the preparation of compounds comprising a terpenoid core or scaffold, such as 6/7/5 tricycloalkanes. The disclosed methods utilize abundant starting materials and simple reaction sequences that can be used to tunably and scalably assemble common terpenoid cores. In various aspects, the present disclosure pertains to compounds prepared using the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.

First claim

What is claimed is:

1. A compound, wherein the compound has a formula represented by a structure selected from:

wherein E is —(C═O)OR 10 , wherein R 10 is C1-C6 alkyl;
wherein each of R 1b and R 1d is independently hydrogen, C1-C6 alkyl, aryl, or —(CH 2 ) m (C═O)OR 11 , wherein m is an integer selected from 0, 1, 2, and 3, and wherein R 11 is C1-C6 alkyl;
wherein R 2 is hydrogen, C1-C6 alkyl, aryl, or —(CH 2 ) n (C═O)OR 12 , wherein n is an integer selected from 0, 1, 2, and 3, and wherein R 12 is C1-C6 alkyl;
wherein A 1 is —C(R 20 )(R 21 )—, —NR 22 — or —CH 2 —, wherein R 20 is hydrogen, C1-C6 alkyl, or —(CH 2 ) p (C═O)OR 30 , wherein R 30 is C1-C6 alkyl; and wherein p is an integer selected from 0, 1, 2, and 3, wherein R 21 is hydrogen, C1-C6 alkyl, or —(CH 2 ) q (C═O)OR 31 , wherein R 31 is C1-C6 alkyl; and wherein q is an integer selected from 0, 1, 2, and 3, and wherein R 22 is C1-C6 alkyl, or —(C═O)OR 32 ; and wherein R 32 is C1-C6 alkyl.

2. The compound of claim 1 , wherein E is —(C═O)OCH 3 .

3. The compound of claim 1 , wherein each of R 1b and R 1d is independently hydrogen, methyl, phenyl, or —CH 2 (C═O)OCH 3 .

4. The compound of claim 1 , wherein R 2 is hydrogen, methyl, phenyl, or —CH 2 (C═O)OCH 3 .

5. The compound of claim 1 , wherein A 1 is —CH 2 — or —CHCH 3 .

6. The compound of claim 1 , wherein the compound has a formula represented by structure:

7. The compound of claim 1 , wherein the compound has a formula represented by structure:

8. The compound of claim 1 , wherein the compound has a formula represented by structure:

9. The compound of claim 1 , wherein the compound has a formula represented by structure

10. The compound of claim 1 , wherein the compound has a formula represented by structure:

11. The compound of claim 1 , wherein the compound has a formula represented by structure:

12. The compound of claim 1 , wherein the compound has a formula represented by structure:

13. The compound of claim 1 , wherein the compound has a formula represented by structure:

14. The compound of claim 1 , wherein the compound has a formula represented by structure:

15. The compound of claim 1 , wherein the compound has a formula represented by structure:

16. The compound of claim 1 , wherein the compound has a formula represented by structure

17. The compound of claim 1 , wherein the compound has a formula represented by structure:

18. The compound of claim 1 , wherein the compound has a formula represented by structure:

19. The compound of claim 1 , wherein the compound has a formula represented by structure:

Assignees

• Univ Florida

Inventors

• Grenning Alexander James
• Scott Sarah

Classifications

• C07D211/72

  with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms · CPC title

• C07C253/30 Primary

  by reactions not involving the formation of cyano groups · CPC title

• C07D211/70 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07C255/47

  to carbon atoms of rings being part of condensed ring systems · CPC title

• C07C2603/78

  containing seven-membered rings · CPC title