Total Synthesis of Aplysiasecosterol A

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1. Total Synthesis of Aplysiasecosterol A
2. Figure 2. Retrosynthetic analysis of aplysiasecosterol A
3. Scheme 1. Preparation of the Left-Hand Segment 9
4. Scheme 2. Devised Desymmetrizing Lactolization ProcessScheme 3. Two-Step Synthesis of 22
5. Scheme 4. First Route to the Right-Hand Segment 10
6. Scheme 5. Second Route to the Right-Hand Segment 10
7. Scheme 6. Completion of the Synthesis of Aplysiasecosterol A (1)
8. Table 2. Conditions for the HAT Based
9. Table 3. Cyclization of the Analogues of
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Figure 2. Retrosynthetic analysis of aplysiasecosterol A (1).Table 1. Studies of 2-Bromoallylation of Aldehyde 17a4 Å molecular sieves. bSonication.

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Слайд 1Total Synthesis of Aplysiasecosterol A
Figure 1. Aplysiasecosterol A (1) and

related secosteroids.

Слайд 2Figure 2. Retrosynthetic analysis of aplysiasecosterol A (1).
Table 1. Studies

of 2-Bromoallylation of Aldehyde 17
a4 Å molecular sieves. bSonication.

Figure 2. Retrosynthetic analysis of aplysiasecosterol A (1).Table 1. Studies of 2-Bromoallylation of Aldehyde 17a4 Å molecular

Слайд 3Scheme 1. Preparation of the Left-Hand Segment 9

Слайд 4Scheme 2. Devised Desymmetrizing Lactolization Process
Scheme 3. Two-Step Synthesis of

Scheme 2. Devised Desymmetrizing Lactolization ProcessScheme 3. Two-Step Synthesis of 22

Слайд 5Scheme 4. First Route to the Right-Hand Segment 10

Слайд 6Scheme 5. Second Route to the Right-Hand Segment 10

Слайд 7Scheme 6. Completion of the Synthesis of Aplysiasecosterol A (1)

Слайд 8Table 2. Conditions for the HAT Based Radical Cyclization of

8
aThe solvents were subjected to freeze−pump−thaw cycling except for entry

1. VEtOH:V(CH2OH)2 = 4:1, unless otherwise noted. All reactions were complete in 1 h. bDetermined by 1H NMR analysis of the mixture.
c1.0 equiv. [Fe], 2.5 equiv. [Si]. d0.50 equiv. [Fe], 2.5 equiv. [Si].
e0.50 equiv. [Fe], 5.0 equiv. [Si].
fVEtOH:VDCE:V(CH2OH)2 = 3:1:1.

Table 2. Conditions for the HAT Based Radical Cyclization of 8aThe solvents were subjected to freeze−pump−thaw cycling

Слайд 9Table 3. Cyclization of the Analogues of 8 under the

Optimal Conditionsa
aThe solvents were subjected to freeze−pump−thaw cycling. 0.50 equiv.

[Fe], 5.0 equiv. [Si]. VEtOH:VDCE:V(CH2OH)2 = 3:1:1, 60 °C. All reactions were complete in 1 h.
bThe ratio of the desired product and the other three isomers. Determined by 1H NMR analysis of the mixture.

Table 3. Cyclization of the Analogues of 8 under the Optimal ConditionsaaThe solvents were subjected to freeze−pump−thaw

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Total Synthesis of Aplysiasecosterol A

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Слайд 1Total Synthesis of Aplysiasecosterol A
Figure 1. Aplysiasecosterol A (1) and

related secosteroids.

Слайд 2Figure 2. Retrosynthetic analysis of aplysiasecosterol A (1).
Table 1. Studies

of 2-Bromoallylation of Aldehyde 17
a4 Å molecular sieves. bSonication.

Слайд 3Scheme 1. Preparation of the Left-Hand Segment 9

Слайд 4Scheme 2. Devised Desymmetrizing Lactolization Process
Scheme 3. Two-Step Synthesis of

Слайд 5Scheme 4. First Route to the Right-Hand Segment 10

Слайд 6Scheme 5. Second Route to the Right-Hand Segment 10

Слайд 7Scheme 6. Completion of the Synthesis of Aplysiasecosterol A (1)

Слайд 8Table 2. Conditions for the HAT Based Radical Cyclization of

8
aThe solvents were subjected to freeze−pump−thaw cycling except for entry

Слайд 9Table 3. Cyclization of the Analogues of 8 under the

Optimal Conditionsa
aThe solvents were subjected to freeze−pump−thaw cycling. 0.50 equiv.

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Total Synthesis of Aplysiasecosterol A

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Слайд 1Total Synthesis of Aplysiasecosterol AFigure 1. Aplysiasecosterol A (1) and

related secosteroids.

Слайд 2Figure 2. Retrosynthetic analysis of aplysiasecosterol A (1).Table 1. Studies

of 2-Bromoallylation of Aldehyde 17a4 Å molecular sieves. bSonication.

Слайд 3Scheme 1. Preparation of the Left-Hand Segment 9

Слайд 4Scheme 2. Devised Desymmetrizing Lactolization ProcessScheme 3. Two-Step Synthesis of

Слайд 5Scheme 4. First Route to the Right-Hand Segment 10

Слайд 6Scheme 5. Second Route to the Right-Hand Segment 10

Слайд 7Scheme 6. Completion of the Synthesis of Aplysiasecosterol A (1)

Слайд 8Table 2. Conditions for the HAT Based Radical Cyclization of

8aThe solvents were subjected to freeze−pump−thaw cycling except for entry

Слайд 9Table 3. Cyclization of the Analogues of 8 under the

Optimal ConditionsaaThe solvents were subjected to freeze−pump−thaw cycling. 0.50 equiv.

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Слайд 1Total Synthesis of Aplysiasecosterol A
Figure 1. Aplysiasecosterol A (1) and

Слайд 2Figure 2. Retrosynthetic analysis of aplysiasecosterol A (1).
Table 1. Studies

of 2-Bromoallylation of Aldehyde 17
a4 Å molecular sieves. bSonication.

Слайд 4Scheme 2. Devised Desymmetrizing Lactolization Process
Scheme 3. Two-Step Synthesis of

8
aThe solvents were subjected to freeze−pump−thaw cycling except for entry

Optimal Conditionsa
aThe solvents were subjected to freeze−pump−thaw cycling. 0.50 equiv.