Methods and compositions for terpenoid tricycloalkane synthesis
AssigneeUniversity of Florida Research Foundation, Inc.
InventorsAlexander James Grenning, Sarah Scott
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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.
Claims17
A compound, wherein the compound has a formula represented by a structure:
- wherein E is —(C═O)OR10, wherein R10 is C1-C6 alkyl;
- wherein each of R1a, R1b, R1c, and R1d is independently hydrogen, C1-C6 alkyl, aryl, or —(CH2)m(C═O)OR11;
- or wherein R1a and R1c are covalently bonded and, together with more intermediate carbons, comprise —CH2CH2—, or —CH═CH—, wherein m is an integer selected from 0, 1, 2, and 3;
- and wherein R11 is C1-C6 alkyl;
- wherein R2 is hydrogen, C1-C6 alkyl, aryl, or —(CH2)n(C═O)OR12, wherein n is an integer selected from 0, 1, 2, and 3;
- and wherein R12 is C1-C6 alkyl;
- wherein A1 is —C(R20) (R21)—, wherein R20 is C1-C6 alkyl, or —(CH2)pC═O)OR30, wherein R30 is C1-C6 alkyl, wherein p is an integer selected from 0, 1, 2, and 3, wherein R21 is hydrogen, C1-C6 alkyl, or —(CH2)qC═O)OR31, wherein R31 is C1-C6 alkyl, and wherein q is an integer selected from 0, 1, 2, and 3.
A compound, wherein the compound has a formula represented by a structure:
- wherein E is —CN or —(C═O)OR10;
- wherein R10 is C1-C6 alkyl;
- wherein each of R1a, R1b, R1c, and R1d is independently hydrogen, C1-C6 alkyl, aryl, or —(CH2)m(C═O)OR11, or wherein R1a and R1c are covalently bonded and, together with more intermediate carbons, comprise —CH2CH2—, or —CH═CH—, wherein m is an integer selected from 0, 1, 2, and 3, and wherein R11 is C1-C6 alkyl;
- wherein R2 is hydrogen, C1-C6 alkyl, aryl, or —(CH2)n(C═O)OR12, wherein n is an integer selected from 0, 1, 2, and 3, and wherein R12 is C1-C6 alkyl;
- wherein A1 is —NR22—, wherein R22 is C1-C6 alkyl, or —(C═O)OR32;
- and
- wherein R32 is C1-C6 alkyl.
A compound, wherein the compound has a formula represented by a structure:
- wherein E is —(C═O)OR10, wherein R10 is C1-C6 alkyl;
- wherein each of R1a, R1b, R1c, and R1d is independently hydrogen, C1-C6 alkyl, aryl, or —(CH2)m(C═O)OR11;
- or wherein R1a and R1c are covalently bonded and, together with more intermediate carbons, comprise —CH2CH2—, or —CH═CH—, wherein m is an integer selected from 0, 1, 2, and 3;
- and wherein R11 is C1-C6 alkyl;
- wherein R2 is hydrogen, C1-C6 alkyl, aryl, or —(CH2)n(C═O)OR12, wherein n is an integer selected from 0, 1, 2, and 3, and wherein R12 is C1-C6 alkyl;
- wherein A1 is —C(R20)(R21)—, —NR22— or —CH2—, wherein R20 and R21 are each independently selected from:
- hydrogen, C1-C6 alkyl, or —(CH2)pC═O)OR30;
- wherein R30 is C1-C6 alkyl;
- and wherein p is an integer selected from 0, 1, 2, and 3;
- and wherein R22 is C1-C6 alkyl, or —(C═O)OR32;
- and wherein R32 is C1-C6 alkyl.
A compound, wherein the compound has a formula represented by a structure:
- wherein E is —CN or —(C═O)OR10, wherein R10 is C1-C6 alkyl;
- wherein each of R1a, R1b, R1c, and R1d is independently hydrogen, C1-C6 alkyl, aryl, or —(CH2)m(C═O)OR11;
- or wherein R1a and R1c are covalently bonded and, together with more intermediate carbons, comprise —CH2CH2—, or —CH═CH—, wherein m is an integer selected from 0, 1, 2, and 3;
- and wherein R11 is C1-C6 alkyl;
- wherein R2 is C1-C6 alkyl, aryl, or —(CH2)n(C═O)OR12, wherein n is an integer selected from 0, 1, 2, and 3, and wherein R12 is C1-C6 alkyl;
- wherein A1 is —C(R20)(R21)—, —NR22— or —CH2—, wherein R20 and R21 are each independently selected from:
- hydrogen, C1-C6 alkyl, or —(CH2)pC═O)OR30;
- wherein R30 is C1-C6 alkyl, wherein if R20 or R21 are H, only one of R20 and R21 is H;
- and wherein p is an integer selected from 0, 1, 2, and 3;
- and wherein R22 is C1-C6 alkyl, or —(C═O)OR32;
- and wherein R32 is C1-C6 alkyl.
A compound, wherein the compound has a formula represented by a structure:
- wherein E is —CN or —(C═O)OR10, wherein R10 is C1-C6 alkyl;
- wherein each of R1a, R1b, R1c, and R1d is independently hydrogen, C1-C6 alkyl, aryl, or —(CH2)m(C═O)OR11;
- or wherein R1a and R1c are covalently bonded and, together with more intermediate carbons, comprise —CH2CH2—, or —CH═CH—, wherein at least one of R1a, R1b, R1c, and R1d is not hydrogen, wherein m is an integer selected from 0, 1, 2, and 3;
- and wherein R11 is C1-C6 alkyl;
- wherein R2 is hydrogen, C1-C6 alkyl, aryl, or —(CH2)n(C═O)OR12, wherein n is an integer selected from 0, 1, 2, and 3, and wherein R12 is C1-C6 alkyl;
- wherein A1 is —C(R20)(R21)—, —NR22— or —CH2—, wherein R20 and R21 are each independently selected from:
- hydrogen, C1-C6 alkyl, or —(CH2)pC═O)OR30;
- wherein R30 is C1-C6 alkyl, wherein if R20 or R21 are H, only one of R20 and R21 is H;
- and wherein p is an integer selected from 0, 1, 2, and 3;
- and wherein R22 is C1-C6 alkyl, or —(C═O)OR32;
- and wherein R32 is C1-C6 alkyl.
Dependencies are inferred from the claim text.